


South Side

by jensenisafallenangel



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Angst, Angst with a Happy Ending, Bad Boy Dean, Bisexual Dean Winchester, Bottom Dean, Canon-Typical Violence, Chicago (City), Drugs, Explicit Language, Explicit Sexual Content, First Time, Friends to Lovers, Gambling, Gang Violence, Grey-Asexual Castiel (Supernatural), Henriksen/Mills are a cop duo, Hurt Castiel, Hurt Dean Winchester, Hurt/Comfort, M/M, Minor Character Death, Organized Crime, Partying, Past Castiel/April Kelly, Past Lisa Braeden/Dean Winchester, Police, Prison, Smoking, Street Racing, Top Castiel, Underage Drinking, selling and doing, slight slow burn
Language: English
Status: Completed
Published: 2015-06-16
Updated: 2015-09-05
Packaged: 2018-04-04 17:35:49
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 15
Words: 85,975
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4146711
Author URL: https://archiveofourown.org/users/jensenisafallenangel/pseuds/jensenisafallenangel
Summary: <blockquote class="userstuff">
              <p>Castiel Novak is in trouble with the police, again, but they offer him a way out. To avoid jail, he becomes an informant in a gang where he meets Dean, a street smart bad boy. At first glance, Castiel wants nothing to do with him but that changes and before he knows it, Castiel is thrown into a dangerous world where he has to choose who wants to protect. Himself or Dean?</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> My tumblr: jensenisafallenangel.tumblr.com
> 
> Enjoy!

Castiel woke up with a stiff neck and a sore back on a very uncomfortable mattress that was definitely not his. He sat up and swung his feet over the edge to place them flat on the floor which made his stomach churn at the movement. His dark brown hair always stuck up at weird angles when he woke up so he raised a hand to smooth it out as he looked around.

 _Shit_ , he thought as he slowly started to remember why he was in a tiny jail cell.

“Oh good, you’re up,” Castiel heard someone say. 

The black cop that had helped arrest Castiel last night stood outside of the cell with crossed arms and a smug smile. His name was maybe Henderson or Henricks or something, Castiel couldn’t recall. He struggled to remember anything with the pounding headache that accompanied his hangover. 

Castiel squinted up at the officer through the harsh fluorescent lights. “Can I go yet?”

“Nope. You’re going to tell my partner and I what happened last night.”

Castiel groaned and closed his eyes again. He could hear the door to his cell being opened and then he was pulled roughly to his feet which did no favors for his uneasy stomach. He focused on not throwing up. There wasn’t much in his stomach and he couldn’t remember the last time he ate something.

The officer, whose name still escaped Castiel, led him to a small, windowless interrogation room. Castiel sat down before he realized another cop already sat at the table. She had very short brown hair and smiled at Castiel. Her smile was kind, unlike the officer who dragged him in here.

 _Was she there last night?_ Castiel couldn’t remember.

“Castiel, why don’t you tell us what happened?” she asked. 

Castiel read “Mills” on her blue Chicago police uniform’s nametag. 

“Officer Mills,” Castiel started, rubbing his temples with both hands, “can I have some water, please?” She looked at the cop that brought him into the room and nodded. He left.

“Thanks,” Castiel said.

“Not a problem,” she answered. She had a file in front of her on the table and opened it. “So, this isn’t the first time you’ve been in trouble, right?”

Castiel just shook his head. The door opened and the other cop returned. Castiel nodded his thanks before chugging the whole cup. He felt marginally better.

“Now,” Officer Mills continued, “Officer Henriksen and I don’t think you were the one responsible for last night.”

Castiel just raised his eyebrows. He set the cup down and leaned back in his chair. He would have crossed his arms if they hadn’t been handcuffed for the walk over and attached to a metal ring on the table.

“We think this was your brother’s doing but he got away before we could catch him,” Henriksen said, sitting next to Mills across from Castiel, who didn’t say anything.

“Was he behind the other stuff on your sheet, too?” Henriksen said. “You don’t exactly look a stoner or a thief.”

“You don’t know anything about me,” Castiel said icily, meeting Henriksen’s eyes with a glare across the table.

“Look, we’re trying to help,” Mills said, breaking the tension. Castiel shifted his eyes over and eased up on the glare. 

“I understand but I stole that car last night, I shoplifted and the weed was mine. My brother had nothing to do with it, any of it,” Castiel argued even if it wasn’t the whole truth. 

“I don’t think someone who attended such a prestigious college prep school would be so stupid,” Henriksen said.

“Key word being ‘attended.’ It might not be in your little file, but they kicked me out. They didn’t want someone who was in juvenile detention for drugs and fighting.”

“Fighting? What happened?” Officer Mills asked sincerely. 

“Misunderstanding at school,” Castiel shrugged. 

Henriksen and Mills shared a look. 

“You know, normally grand theft auto would scare people. It’s a considerable amount of jail time. Especially for someone with a record,” Henriksen pointed out.

Castiel swallowed and looked down at his handcuffed hands. This situation wasn’t new to him and he could handle it. He just needed to stay calm and think of a plan.

“We know you’re smart and you seem like a good guy,” Mills said and Castiel scoffed to himself. He wouldn’t say the same thing. “We might have a way to help you if you help us.”

“How would you like to be an informant?” Henriksen asked. Castiel looked up, confused. 

“We’re working on getting information on a gang. They’re small time, not a lot of guys, and they just sell weed. However, we’ve been trying to bring some of them in and we could use you,” Mills explained. “We don’t normally use civilians for something like this but we’re running out of options.”

“Isn’t it dangerous to join and snitch on a gang?” Castiel asked doubtfully.

“We’ll keep you safe,” Mills reassured him. “We just want you to have another option besides jail. You’re only twenty and like I said, we want to help.”

Castiel considered it for a moment. It wouldn’t be fair for him to go to jail because stealing the car was his brother, Gabriel’s, idea. He was lying to protect him. Again. Castiel had covered for Gabriel for the shoplifting and the weed was thrown to him because Gabriel couldn’t get caught with it again. Family always came first but that didn’t mean Castiel needed to go to jail and they still couldn’t prove Gabriel had anything to do with last night. Castiel knew talking to the cops was one of the worst things he could do, growing up where he did taught him that, and working with them would be worse if anyone ever found out. Jail didn't seem like too hot of an option either, though. Reluctantly, he decided to take the deal. 

“Fine,” Castiel agreed. “What do I have to do?”

 

~~~

 

Castiel walked through the front door of his apartment after his rough night and morning of signing a risky deal. He really wasn’t in the mood to have to deal with Gabriel. They shared an apartment and he loved his brother, he did, but the guy was a handful to say the least. 

“Castiel, man, where have you been?” Gabriel asked, pulling him into a hug that Castiel barely returned.

“Covering for you. Again,” Castiel said as he broke the hug. Gabriel’s face fell.

“Hey, I’m sorry. I couldn’t get caught doing something stupid. You know that I’m on probation,” Gabriel stated.

“Yeah, well you’re lucky I’m not. Or going to jail,” Castiel said as harshly as possible. 

Gabriel didn’t say anything but Castiel could see he felt guilty. 

“I’m going to bed. I didn’t sleep very well in a jail cell last night,” Castiel snapped.

He slammed his bedroom door shut leaving Gabriel standing alone in their living room. 

 

~~~

 

Dean Winchester blinked awake as his alarm blared before slamming the clock on the bedside table to turn it off. He sat up and threw his legs over the edge of the bed as he rubbed sleep out of his eyes and saw that the clock read eight AM in searing red numbers.

He shuffled out of his small bedroom towards the combined kitchen and eating area across the living room from his room. The apartment’s other bedroom and single bathroom were on Dean’s right as he headed towards food and coffee with the front door on his left. He passed the crappy, old plaid sofa and run-down TV as he sighed from being up so early.

The apartment’s other occupant had already made coffee for the both of them. 

_He is way too happy to be awake this early_ , Dean thought about his brother, Sam. 

“Morning,” Sam smiled. Dean just grunted and accepted the cup of black coffee handed to him. 

“Why are you up so early?” Dean asked, finally starting to actually wake up. “It’s a freaking Saturday, Sam.”

“It’s late May, finals are coming up,” Sam said, like it was obvious. 

“And?”

“You are so not a morning person,” Sam laughed. “A bunch of us are getting together to study at the library,” 

“You and only you would be happy about that,” Dean teased, taking a long drink of coffee. “But someone’s gotta be the brains of this family and it sure ain’t me.”

Sam always took school seriously, the opposite of Dean who didn’t even finish high school. Not that it mattered since he didn’t need it anyways. 

“Would you be able to drop me off before you go to work?”

“Sure,” Dean said, “is that one girl going to be there?”

“Who, Jessica?” Dean nodded. “Maybe.”

“You’re not studying at all, are you?” Dean smirked, finishing his coffee.

“Shut up,” Sam said with a laugh. “Can you take me?”

“Yeah, let me get dressed and we can go,” Dean got up, put his mug in the sink and headed to his room to change. 

 

~~~

 

Once Sam was at the library to supposedly study, Dean headed to work at Singer Auto. It served as a constant reminder of his father, John, who used to co-own the place before he died. Dean learned everything he knew about working on cars at this garage. 

While Sam had excelled at school, this was much more Dean’s strong suit. He was made to fix and build, to get his hands dirty.

“Hey, Bobby,” Dean greeted as he walked into the shop. 

“Ready to get to work?” came the gruff reply from Bobby Singer, the current sole owner. He was in his office, behind his desk, wearing his trademark baseball hat with the garage’s logo. 

Dean smiled. He was always ready to work on cars, letting the job take him over as hours flew by.

This particular Saturday wasn’t too busy so Bobby let Dean go at two. He shouted bye to Bobby, grabbed his leather jacket and headed to his 1967 Chevy Impala. As much time as he put into the cars at work, he put about ten times more work and love into this car. Besides Sam, this Impala and their crappy apartment was all their dad really left Dean. 

Dean drove to where he usually went after work, a parking lot of a convenience store. A group of guys were already sitting on the curb, or standing, in front of the store. The owner tried to get them to stop hanging around once, since they scared away customers, but a group of guys with guns aren’t easily swayed. 

A few of the guys greeted Dean as he got out of his beloved car and he nodded back. He walked over to one guy and shook his hand.

“Hey, Benny,” Dean said to a man with an old-fashioned hat and a short-trimmed beard.

“How was work?” Benny answered.

“The usual.” To be honest, Benny was the only guy that Dean really liked in this group. The rest were just low-life gang members. 

_You’re not much better_ , Dean thought. The nicer side of his brain chimed in with, “ _You joined for the right reasons_.” 

Dean’s internal moral crisis was interrupted by the gang’s leader, wearing all black and who had an air of power about him. 

“Good, we’re all here,” he said, looking pointedly at Dean. “Now we can get to business. It seems as if someone has been selling on our turf.”

Dean rolled his eyes while some of the guys started yelling and swearing. It just seemed petty to Dean but some of them appeared to actually be offended. Dean couldn’t help the small laugh that escaped. 

“Something funny, Winchester?” the leader asked. 

“No,” Dean said, turning his laugh into a cough.

“We know it was, don’t we?” he continued. “Why don’t we find some of them and make them pay!”

As the cheers turned to ones of excitement, Dean walked over to the black-clad man to talk. Usually, Dean was the only one to stand up to the guy.

“Are you sure you want to start a war, Crowley?” 

“They’re the ones who want a war,” Crowley argued. 

“Someone’s going to get hurt.”

“You’re going to get hurt,” Crowley said menacingly, getting in Dean’s face, “if you don’t do as I say.”

Dean wasn’t scared of Crowley but he wasn’t going to fight him. He wasn’t worth it.

“I’m just saying…”

“We can’t let those guys sell to our people. Without customers, we have no reason to be here,” Crowley reasoned.

“I don’t care about that. You know why I’m here,” Dean snapped. 

The group had started to pay attention now and had gone quiet. Dean stepped back before it escalated into something no one wanted. 

“All right boys,” Crowley smiled over Dean’s shoulder. “Go kick some ass.”

 

Dean and Benny walked down the street, following Crowley’s orders even though neither of them wanted to. They had been walking for so long it had turned dark. 

“This is bullshit,” Dean spat.

“I know, brother, but it’s what we have to do,” Benny tried to reason. “It’s either we try to find their guys to beat up or we get beat up for not listening.”

Dean didn’t say anything and just took a drag from his cigarette. 

“Besides,” Benny went on, inhaling off his own smoke, “we can’t have anyone else selling to our people, our customers. That’s how we get paid.”

“Speak for yourself, I have a real job,” Dean countered.

“So do I, the diner, but extra money never hurt anyone,” Benny said. Dean couldn’t argue against that and kept smoking. “You should back Crowley up, you are his second in command.”

“I never asked to be.”

Both of them finished their cigarettes, crushing the butts under their boots. 

Right when they continued walking, they heard a gunshot that sounded like it came from the street over. They looked at each other and then started running towards the source.

The two immediately stopped running when they heard anguished moans coming from an alley on their right. Both of them cautiously walked in to the dark alley, pulling their guns from the waistbands of their jeans. It wasn’t a pretty sight.

Sitting against the wall of the alley, partially propped up on a dumpster, was one of their own. Jake’s breathing was shallow and both of his hands were covering the lower right side of his abdomen. 

“Benny, call an ambulance,” Dean commanded. He pulled his phone out to do so. “Hey, man, stay with me, you’re going to be fine,” Dean said to Jake, kneeling next to him. “Just keep pressure on it, okay?”

Jake pressed and let out an anguished groan. 

“What happened?” Dean asked.

“Two of them. Had a gun… one tried, to stop… the other. Shot me…while they wrestled… for it,” Jake said weakly, in obvious pain. 

“Michael’s guys?” Dean asked. Jake nodded.

“Which ones?” Benny wanted to know after hanging up despite the dispatcher’s pleas to stay on the line.

“Zac- Zachariah… and Uriel,” Jake said with labored breaths. His eyes started to close.

“Jake!” Dean yelled. “Stay with us, damn it! Where the fuck is the ambulance?” Dean grimaced, looking behind him towards the street. As he said that, distant sirens could be heard.

“Jake, they’re almost here, come on, brother. Hold on,” Benny pleaded. Jake’s eyes were closed but there was still a slight rise and fall of his chest.

Dean and Benny walked out of the alley to direct the paramedics into the alley. The ambulance pulled up and two people in all navy hopped out of the back with a medical bag and a stretcher. Dean just pointed into the alley and they headed in.

“You two called?” the driver asked as he hopped down from the front of the ambulance. Dean and Benny nodded. “Stay here, the cops will want to talk to you.”

“You got it,” Dean said. The paramedic followed the other two into the alley. As soon as he left, Dean and Benny walked away. When they heard police sirens, they walked faster. 

“Let’s get everyone to the garage,” Dean suggested. Benny nodded.

 

An hour later, the gang had assembled in Bobby’s garage. Bobby didn’t approve of the gang, or Dean’s involvement, but he knew why he did it so he let them hang out every once in a while after hours. 

“All right, what the hell happened tonight?” Crowley demanded to know.

Dean told everyone that Jake had been shot and by who, leading to cries of outrage. They wanted someone to pay.

“Everyone calm down,” Crowley snapped. They immediately all shut up. “If we’re going to war, we’re going smart. You have to figure they’ll be expecting a hit tonight, in retaliation, right?”

No one answered. 

“So what do we do?” Crowley asked, looking specifically at Dean.

“We wait so they can anticipate an attack,” Dean suggested. “Hit them when they least suspect it.”

“We wait,” Crowley agreed. 

 

Dean finally came home and found Sam on the couch watching T.V. 

“Hey, where’ve you been?” Sam asked. 

“Out,” Dean responded. “How was studying, how’s Jess? You ask her out yet?”

“Don’t change the subject.”

“Did you?”

“No,” Sam sighed, realizing Dean wasn’t giving any other answers to where he had been. “Not yet.”

“Aw come on, Sam!” Dean said, heading to their fridge and grabbing a beer. 

“Wanna grab me one?” Sam asked hopefully.

“Dude, no. You’re barely sixteen,” Dean answered with a small laugh. 

The kid had his birthday a couple weeks ago and Dean wasn’t letting him start down the path everyone else in their neighborhood went down. If anyone was getting out, it was Sam.

“You’re only twenty! And you were drinking at my age, don’t deny it.”

“I’m rounding up,” Dean smirked as he opened the can. “And bite me.”

As if he wanted Sam to do anything he did. He joined Sam on the couch to watch some late night T.V. Dean found it difficult to get what happened tonight out of his mind and to stop worrying about the upcoming war that was sure to erupt. Nothing good would come from it. 

“Dean,” Sam said cautiously. Dean drank his beer and kept his eyes on the T.V. “I know where you were, or at least who you were with. It’s not hard to figure out.”

“What’s your point?” Dean said, sounding exhausted. They had had this argument many times. 

“You know they’re bad news, that’s my point. I don’t want you to get hurt or to get in trouble.”

“I don’t have a choice, Sam.”

“Bullshit, you always have a choice. You taught me that.”

“Not this time,” Dean snapped, finally turning to look at his brother. “I’m doing this to protect you. And Bobby.”

“Really? How?”

Dean sighed and finished his beer. He got up and went to the tiny kitchen, setting the empty can on the counter. He grabbed the last beer from the mostly empty fridge and rejoined Sam. 

“Dean, just talk to me.”

Dean didn’t answer as he sat back down and opened his beer. The two just watched T.V until they were both too tired and Sam didn’t ask Dean anything else before he went to bed. 

 

~~~

 

Castiel sat on a bench along the street trying to be inconspicuous behind a newspaper. Across the street were the two guys he was supposed to talk to. They were about Castiel’s age but seemed older because they were kind of intimidating. They both seemed like the type of guys who knew they were attractive and acted like it.

According to Mills and Henriksen, these two were Dean Winchester and Benny Lafitte. They regularly sold on this corner but no crime had been proven. Yet. The plan was for Castiel to buy some weed from them to start, which shouldn’t be too hard. Or at least that was what Castiel was telling himself. The two guys’ files said they had short criminal histories, nothing serious, but Castiel still was uneasy.

Castiel got up before he could psych himself out and walked over. _Stick to the plan_ , he thought.

 

Dean and Benny stood on the corner, each smoking a cigarette. Castiel opened his mouth to speak but before he could say anything, Dean interrupted him. 

“About time you came over here,” Dean said with a smug half smile. “Hiding behind a newspaper? Really?”

Castiel closed his mouth and felt his cheeks get warm as Benny laughed. 

_Go figure, they’re douchebags_ , Castiel thought. He immediately regretted his decision to help the police.

“You cost me ten bucks. I bet Dean here you’d take ten more minutes to come over here,” Benny said, still smiling. 

“So you want to buy, right?” Dean asked, crushing his cigarette butt under his boot and accepting Benny’s money from the bet.

“Uh, yeah,” Castiel said. It came out weaker than he had hoped. 

“See, here’s the thing,” Dean said, looking right at Castiel. Castiel almost looked away because his gaze was so intense, close to threatening, but he stared right back. “We don’t know you. Or anything about you.”

“We don’t know if we can trust you,” Benny clarified. Castiel nodded his understanding.

“Look, we’re here most days. You’ll just have to come back,” Dean shrugged.

“All right,” Castiel agreed and began to walk away.

“What a weird, dorky guy,” Dean said. He lit another cigarette as he watched Castiel walk away. 

 

Later that day, Castiel met up with Mills and Henriksen at the same precinct where he spent the night a couple nights ago.

“How’d it go?” Mills asked.

“Not very well,” Castiel answered honestly. “They don’t know me, so they don’t want to sell to me yet.”

“So, you have to keep trying,” Henriksen said, “get to know them.”

“Right,” Castiel nodded. It would take some time, but he could easily get to know Dean and Benny, even though they kind of seemed like jerks. 

“All right Castiel, just keep us updated,” Mills said before they walked Castiel out of the building.

 

Castiel returned to a thankfully empty apartment. He, as usual, wasn’t in the mood to deal with Gabriel. He went to his bedroom, kicked his shoes off and flopped back onto his bed. He just started to relax when he heard the front door open.

“Little brother, you home?” Gabriel called. Castiel groaned.

“I’m younger, not little.”

Gabriel appeared in the door to Castiel’s bedroom. “You left before me this morning, what were you up to?”

“That’s not surprising, you usually sleep late,” Castiel argued. 

“That’s fair,” Gabriel agreed. He popped a lollipop into his mouth. “You’re not in trouble for Friday night, are you?”

“It’s fine, Gabriel. I’m not in trouble,” Castiel said, rolling onto his stomach. 

“Because the shoplifting and weed was on me, too. I don’t want to ruin your life more. I know the fight wasn’t your fault either, that was because of…”

“Gabriel,” Castiel snapped, “I’m fine, everything’s fine.” He grumbled the last part into his pillow. Castiel really didn’t want to go there. Gabriel left and Castiel drifted into a fitful sleep. 

 

~~~

 

Dean woke up the next Saturday, again at 8 AM, and headed to work. He got lost in his work, fixing car after car, until Bobby told him he could go.

After work, he drove to the usual parking lot to meet up with the guys. Immediately, Dean noticed someone who hadn’t been around in a week. 

“Jake!” Dean exclaimed, getting out of his Impala. He walked over and shook his hand. “Welcome back, man.”

“Thanks, Dean. And thanks for being there, calling an ambulance and everything,” Jake said.

“Of course. Cops didn’t give you too hard of a time I hope?”

“Nothing I couldn’t handle,” Jake grinned. 

“Boys,” Crowley said, interrupting the reunion and getting everyone’s attention. “Tonight, we’re having a party, at my place of course.”

Dean rolled his eyes. Crowley thought his house was hot shit but it wasn’t anything special. It was just better than what anyone else had. The south side of Chicago definitely wasn’t known for its housing.

“Since it seems Michael is gearing up his boys for a good old-fashioned turf war,” Crowley paused, “we’re going to need numbers. Bring some friends by.”

They guys all started talking when Crowley was done. Dean turned to Benny.

“What about the guy who keeps trying to buy from us?” Dean asked. 

The same guy had come back on Wednesday and they told him pretty much the same thing, they didn’t know him and they didn’t sell to people they didn’t trust. Dean and Benny both admired his persistence though. 

“He’s still weird, but what the hell. Let’s go to our usual spot and see if he shows.”

 

Sure enough, there he sat on his regular bench. He was already there when Dean and Benny showed up at their usual position and waited for him to come over.

“Hey man,” Benny greeted. Cas nodded.

“We have a chance for you to get to know us, our whole crew. You feeling like a party tonight?”

“Sure,” Castiel said, slightly worried. They sold drugs so he was afraid of something crazy. 

“All right then,” Dean said, lighting a cigarette. “What’s your name, anyways?”

“Castiel,” Castiel said. Dean raised his eyebrows but didn’t say anything about the unusualness of the name. 

“I’m Dean, this is Benny,” Dean said, barely attempting to blow his smoke away from Castiel’s face.

Castiel coughed a little as Benny told Castiel Crowley’s address and time to show up.

“We’ll see you later,” Dean dismissed and Castiel left. 

Benny smiled as he took a drag from his cigarette.

“What?” Dean snapped, inhaling of his own.

“I don’t know if that’s the kind of guy Crowley was looking for in his little pissing match with Michael, brother.”

“Well, we want to bring someone. If he’s not cut out then he just gets to come to a party, all right?”

“All right,” Benny agreed. 

 

Castiel got home and found Gabriel making something that smelled delicious in their kitchen. He flopped on the couch and closed his eyes. 

_Holy shit,_ Castiel thought, _I got invited to a party by gangbangers._

__

“Where’ve you been, little brother?” Gabriel wondered. 

__

“Out,” Castiel replied. 

__

“Obviously,” Gabriel rolled his eyes. “I meant where. Are you getting into shenanigans? You know how I feel about shenanigans, I want to be taken with.”

__

Castiel just sighed. 

__

“Whatever. What are you doing tonight?” Gabriel asked.

__

“Going to a party, surprisingly enough.”

__

Gabriel choked on a sample of whatever he made.

__

“Wha---a what? Se- Seriously?” he stuttered, trying to breathe and talk.

__

“Yes.”

__

“Can I come?”

__

“No.”

__

“Why not?”

__

“I don’t think I get a plus 1.”

__

“Maybe I know them.”

__

“Trust me, you don’t.”

__

“Come on, Cassie!”

__

“Gabe, just drop it.” 

__

And surprisingly, he did. 

__

 

__

Castiel shared a slightly tense dinner with Gabriel. The casserole was amazing which didn’t surprise Castiel. Gabriel had always been a foodie and could cook like a pro. When Castiel had done the dishes and thanked Gabriel, he headed to his room to call Officer Jody Mills.

__

“Hello?”

__

“Officer Mills? It’s Castiel Novak.”

__

“Is everything okay?” was her worried response.

__

“Yeah, I’m fine. Dean and Benny invited me to a party. Should I go?”

__

“Sure, this is good. You can get close to all of them and get information. Just promise me one thing.”

__

“What’s that?”

__

“Try not to get in trouble? Be careful.”

__

“I’ll try. Thanks,” Castiel said before hanging up. 

__

He felt a pang of sadness at Jody’s obvious “mom voice.” He started to think about his own mom, the few memories he had of her, but he promised himself he wouldn’t do that anymore. He plugged in some earbuds and lost himself in his music. 

__

 

__

A pounding on his door woke Castiel up. He checked his watch and it read 10 o’clock. Shit, he thought. It was dark out and Dean told him to show a half hour ago.

__

“Don’t you have a party to get to?” Gabriel asked through the door as Castiel yanked his earbuds out. 

__

“Yeah, thanks,” Castiel called back. 

__

He quickly got ready, keeping his same dark jeans on, his favorite pair, but changed into a plaid button-up with different shades of blue. There was no hope for his bed head so he just left it sticking up everywhere. 

__

Castiel walked into the living room and found Gabriel on the couch in jeans and a simple black shirt. 

__

“You have plans for tonight?” Castiel asked. 

__

“Why yes, I do. Thanks for asking,” Gabriel answered. 

__

“Are you going to tell me what they are?”

__

“Nope. But have fun! Don’t do anything I wouldn’t do.”

__

“There isn’t anything you wouldn’t do, Gabriel.”

__

Gabriel’s response was his signature eyebrow wiggle. Castiel rolled his eyes and exited the apartment. He walked down the street towards the address he was given with a weird mixture of excitement and fear. This was new territory for him and he didn’t know what to expect. Anyone could be at this party. Maybe Dean and Benny didn’t have dangerous records but other people might.

__

 

__

Castiel showed up to a party already in progress. It was warm out so people were scattered on the lawn as well as on the porch and in the house. The house was simple but run-down, white and one story. 

__

He quickly swallowed his fear and walked towards the house. Everyone he passed had either a red Solo cup or a bottle of beer in their hand and seemed to be eyeing him up and down. For the most part, they seemed curious but not malicious. 

__

A guy who seemed to be acting as a bouncer stepped in front of Castiel as reached the front door to the house. He had an coy grin that made him look like he wanted to eat Castiel. It was unsettling. He was also trying to be intimidating except he was about Castiel’s height so it wasn’t working. 

__

“Can I help you?” the guy sneered. 

__

“I’m…” Castiel started. 

__

“It’s cool,” Dean said as he stepped out of the house from behind the asshole. “He’s with me.” He walked outside and put an arm around Castiel. Dean didn’t seem drunk but he smelled like booze.

__

“Really?” the jerk asked.

__

“Yes. You don’t always have to be such a dick,” Dean laughed. “Dick.”

__

Dean kept laughing at his own joke and Dick, Castiel guessed that was his name, glared.

__

“I’ve been waiting for ya, Cas,” Dean said, guiding him into the house. “Where’ve ya been?”

__

“I, uh, fell asleep,” Castiel answered, looking around the house and deciding to ignore the nickname Dean gave him who was busy laughing at Castiel’s answer. Everyone else had drinks and stayed focused on their conversations. 

__

The two reached the kitchen and Dean took his arm off of Castiel’s shoulders. Benny was standing there with a brunette on his arm who was introduced to Castiel as Andrea. After they had been introduced, Benny and Andrea wandered off.

__

Dean tried to hand Castiel a cup of the same thing he was drinking.

__

“Oh, no thanks. I don’t really…”

__

“What, drink? Come on, sure you do!” Dean exclaimed.

__

Castiel looked down. He didn’t really and would prefer not to, especially since the last time he did, he got arrested for stealing a car that Gabriel had actually stolen.

__

“One drink, Cas. No harm in one little drink,” Dean teased, pushing the cup into his hand with a smile.

__

Castiel broke down and took the cup and sipped from it. It was strong, maybe too strong, but it was hard to say no to Dean and his slightly intoxicated goofy smile and vivid green eyes. Castiel took another drink, a bigger one, to shut his brain up.

__

Dean kept smiling and threw his arm around Castiel again. This side of Dean was a lot nicer than the asshole he had met on the street.

__

“There’s someone you gotta meet, man,” Dean said, maneuvering them into the living room. They made it through the crowd of people, both managing to not spill their drinks. The two of them stopped in front of a couch.

__

On the couch was a guy with a girl on either side of him. Castiel recognized Crowley from the police files he had to pretend to know nothing about. It had his first name but Castiel couldn’t remember it. 

__

“Crowley, I brought a guest for you to meet,” Dean said, taking Crowley’s attention away from the girls. He stood up.

__

“Crowley. Pleasure. And you are?” he said, extending a hand.

__

“Castiel,” he managed, shaking Crowley’s hand. It was a little intimidating to be examined under dark, searing eyes of a gang leader in all black.

__

“You seem a little too goody-goody to be hanging around with us,” the dark haired girl on the couch said. The blonde girl just smiled. “Like an angel amongst devils.”

__

“Shut up, Meg,” Crowley snapped before turning his attention back to Castiel. “Well, it was nice to meet you Castiel. I hope we see you around more,” Crowley finished with a bemused smirk.

__

“Bye, Clarence,” Meg said, earning a glare from Crowley.

__

“Let’s go outside,” Dean said into Castiel’s ear because the song changed and someone cranked it up, making it impossible to talk. 

__

On the back deck, there were a lot less people and it was much quieter. The two of them walked to the edge of the deck and leaned on the railing.

__

“Why’d she call you Clarence?” Dean wondered.

__

“He’s the angel from _It’s a Wonderful Life_ ,” Castiel said. 

__

Dean just shrugged like he still didn’t get it. Cas was going to explain but Dean continued.

__

“She must like you,” Dean smiled, “she already gave you a nickname.”

__

“Lucky me,” Castiel said. He gave it some more thought. “Didn’t you give me a nickname, too?”

__

“Very observant, Cas.”

__

Castiel didn’t really know what to say to Dean so he was glad when Dean pulled out his pack of cigarettes from the back pocket of his jeans. It seemed like Dean was flirting but Castiel figured he was imagining it. He didn’t normally get flirted with so it was hard to tell. Dean was probably just being nice and the alcohol helped loosen him up. It didn’t make sense for Dean to be flirting with him so he ignored it. 

__

“You smoke?” he asked. Castiel shook his head.

__

He pulled his lighter out of his front pocket and lit one. He took a long drag and turned his head to the left to blow the smoke away from Castiel. 

__

“So, Cas, how did you come to find Benny and me on that street corner? Usually you gotta know somebody.”

__

“Oh, the usual way I guess. Asked around?” Castiel answered, the last word coming out like a question. 

__

He knew he sounded like an idiot and he guessed he did because Dean laughed but it wasn’t in a mocking way so Castiel laughed too. 

__

They both kept working on their drinks, Dean also on his cigarette, as they stood in a comfortable silence next to each other. Then, there was a commotion that seemed to be coming from the front of the house. 

__

Several people were exiting out of the house, off the deck and towards the gate at the edge of the small yard and into an alley. 

__

Dean set his drink down and put his cigarette out under his boot on the deck. Castiel followed suit with his drink and followed Dean back into the house without either saying anything. 

__

They passed more people leaving the opposite way as they headed towards the source of the problem. 

__

In the front yard there seemed to be a stand-off between Crowley and his guys and another group. Castiel could recognize Crowley’s guys from the police files. It was pretty dark and hard to see the other group of guys. The closest street light was busted and Crowley’s porch light didn’t do much.

__

Castiel stayed in the house on Dean’s orders as Dean sauntered onto the front lawn to join his gang. 

__

“What do _you_ want, Michael?” Crowley snarled, talking to the guy who looked in charge of what Castiel could only assume was a rival gang. Castiel was trying to see what was going on but stay unseen. This was _not_ part of the deal he made with the police. One gang was fine but not two. This was too dangerous.

__

“Well, your boys beat up Raphael last weekend. We’re here to return the favor,” came a cool, snide reply from the rival gang’s dark haired leader. 

__

“They beat him up because your guys shot Jake,” Crowley pointed out, crossing his arms over his chest. 

__

“YOU guys were strolling, looking for a fight,” Michael said at the same volume but angrier. 

__

“You sold on OUR turf!” Crowley shouted. Crowley’s guys were getting angrier as well and started yelling and cursing. A few guys on each side were stepping closer and closer. 

__

Castiel couldn’t see which side threw the first punch but it suddenly became an all-out brawl. Crowley got hit with a nice right hook from Michael, Benny was holding his own against a blond guy in a black v-neck and Dean was in a good spot himself. Castiel saw Dean get socked near his left eye but was clearly winning now. 

__

“That all you got, Uriel?” Dean growled, on top of someone on the ground. He was really beating him, badly, and Castiel almost went out there to stop him when sirens could be heard not too far away. 

__

Without saying a word, every guy on the lawn bolted in a different direction. Dean looked back at the house, saw Castiel and ran towards him. Cas tried not to think too much about Dean running back in for him when he just as easily could have taken off down the street.

__

“Come on, Cas. We gotta go,” Dean said. The two ran through the house, down the back deck’s stairs and out the back gate. 

__

They took off together down the alley and almost made it to the main street when a cop car blocked their way. The blue and red lights were nearly blinding. Castiel barely saw Dean, who was right next to him, but he saw him throw something to his left by the dumpsters. Cas barely registered that fact since there were cops in front of them.

__

A cop yelled, “Freeze!” A hand grabbed Castiel’s and pulled him in the opposite direction down the alley, away from the cops. Castiel blinked away the spots in his eyes and he, of course, was following Dean. 

__

“I bet you’re glad I invited you, huh?” Dean smiled.

__

Castiel smiled back. He wouldn’t change this for anything, it was more fun than he’d had in long time which was telling of how boring things had gotten for him that a gang party disrupted by cops was fun. 

__

That smile faded when another cop car blocked them from going the other way down the alley. They turned around again but the cops from the first car had caught up to them on foot. 

__

“Hands in the air!” one of them yelled.

__

Dean let go of Castiel to put his hands in the air with a smirk. Castiel put his own hands in the air without the same arrogance. 

__

_Not again_ , Castiel couldn’t help but think. 

__

 

__

In the police station, Castiel once again found himself in an interrogation room across from Mills and Henriksen.

__

“This isn’t exactly what we had in mind when we said to infiltrate the gang, Novak,” Henriksen started.

__

“What happened, Castiel?” Mills asked in her usual nice, “mom” voice. Castiel couldn’t help but think that these two had mastered the “good cop/bad cop” routine. 

__

“Crowley’s party was interrupted by a rival gang. The leader’s name was Michael.” 

__

Henriksen and Mills exchanged a look. Castiel leaned forwards in his chair. 

__

“Did you two know about the rival gang?” Castiel accused. 

__

There was a pause and the two officers shared a somewhat guilty look.

__

“Yes,” Henriksen admitted. 

__

“Don’t you think that would be important for me to know? That makes it a lot more dangerous if thugs want to kill me because of who I’m _pretending_ to socialize with!” Castiel snapped, not even trying to hide his anger. 

__

Neither cop said anything. Castiel leaned back in his chair. 

__

“Am I being charged with anything?” he asked.

__

“No,” Mills said gently. 

__

“Fine, I’d like to leave then,” Castiel said, standing up, “call me when you have a better plan.”

__

He left the interrogation room leaving a stunned and silent Mills and Henriksen.

__


	2. Chapter 2

In the lobby of the police station, Dean sat in a plastic chair and holding an ice pack to his left eye. He lowered it and smiled when he saw Castiel.

“That’s quite the shiner you have, Dean,” Castiel said. It already looked nasty, yellow and swollen.

“Thanks, Cas. You should see the other guy,” Dean winked with his good eye and put the ice pack back on the other one. 

“I did,” Castiel said, sitting next to him, “You beat him pretty badly.”

“Fuck yeah I did,” Dean grinned. “Uriel’s a dick.”

“Are you free to go?” Castiel asked.

“Yeah, I’m waiting for Sammy, my brother, to come get me. Kid just got his license.”

Castiel smiled. He could already tell how much Dean loved his little brother. It surely was a much better relationship than Castiel had with Gabriel at the moment.

“Do you want a lift home or whatever?” Dean asked, scratching the back of his neck.

“No, that’s okay. I can walk.”

“Come on, I insist. I invited you to the stupid party and then you got arrested, I feel bad.”

“Good point. All right.”

Dean left the ice pack on the chair on his other side and the two headed outside to wait for Sam.

As Dean was pulling out a cigarette, he told Castiel, “You should hang around with us more, you know how to have a good time.”

Castiel had to laugh. “I didn’t do much but I actually had a good time.”

“Actually?” Dean said with mock hurt. 

“Well, it’s not usually a good thing when the cops show up.”

“I have to agree with you there,” Dean said as he smoked.

The stood quietly for a couple minutes until Dean pointed up the street.

“There’s Sam,” Dean said, crushing the rest of his cigarette under his boot, “come on.”

Sam parked across the street and Dean and Castiel crossed to meet him which was tricky because it was busy even though it was close to one in the morning. The car was old but in great condition. It was long, sleek and black. That’s all Castiel could tell because he didn’t know much about cars.

“Hiya, Sammy,” Dean said, getting in and closing the passenger door, “this is Cas. He needs a lift.”

“Nice to meet you, Cas. I’m Sam, not Sammy,” Sam said as Castiel got into the car behind him.

“Oh, crap. Sam, I lost something,” Dean said as Sam pulled onto the street. 

“Your fighting skills?” Sam asked, pointing at Dean’s black eye.

“No, smart ass. I totally destroyed the other guy, ask Cas.”

Sam looked in the rearview mirror at Cas who shrugged. 

“He ‘totally destroyed the other guy,’” Castiel agreed. 

“Are you mocking me?” Dean accused. Both Sam and Castiel had to laugh.

“Well, I’m glad you two are getting along, but do you have to gang up on me?” Dean grumbled, making the other two just laugh even louder. 

“Did you actually lose something, Dean?” Sam asked seriously when he stopped laughing.

“Yes. Make a right on the next block,” Dean said, grateful the teasing had stopped, at least for now.

Dean directed Sam back to Crowley’s house. 

“Why are we back here?” Castiel wanted to know. 

“Just wait here, okay?” Dean said as Sam parked in front of the house. “Two seconds, promise.”

“Is he usually that vague?” Castiel asked Sam when Dean was out of earshot.

“No,” Sam smiled, “usually it’s worse.”

Castiel looked out the opposite side of the car from where he was sitting at Crowley’s yard. It was still littered with red cups and beer bottles from the party.

“So, Cas, how do you know Dean?” Sam asked after a moment as they waited for Dean to get back. 

“I, uh… we just,” Castiel sputtered. It was hard to explain to Sam, who still seemed like an innocent kid, that he had tried to buy weed from Dean and was trying to get in the same gang. Castiel didn’t know how much Sam knew. 

“All right, I got it,” Dean said, appearing next to the car, making Castiel jump. He didn’t see him sneak up.

Dean’s hand covered the back waistband of his jeans as he climbed into the Impala. Castiel could only assume it was his gun and he had thrown it in the alley when they ran from the cops. 

“All right, we can go,” Dean stated.

“What did you lose, Dean?” Sam asked.

“Nothing, just drive.”

“No, not until you tell me.”

“Sam, can we do this later?” Dean said, shooting a glance back at Castiel.

Sam sighed but must have decided Dean was right and drove away from Crowley’s. It was awkward only for a moment until the radio station they had on came back from commercial.

“ _Journey_? Really?” Sam laughed. His hand went to switch the channel but Dean slapped his hand away. 

“How do you not like _Journey_ , who are you?” Dean joked. 

“I’m driving, I pick the music. That’s _your_ rule! So shut your cakehole.”

“Not if your taste is crap. And she’s still my baby, even if you’re driving. What do you think, Cas, does Sam get to change it?”

“Oh, I don’t know if I want to get in the middle of this,” Cas said to stay neutral. Sam and Dean both laughed and left “Faithfully” on. 

“Right, so where do you live, Cas?” Sam asked. Castiel gave him directions and they were there in a few minutes. They stopped out front of Castiel’s apartment building. 

“You kind of live close, we’re only a few blocks away,” Sam pointed out.

“Thanks for the ride,” Castiel said. Sam nodded. 

“I’m sure I’ll see you soon, Cas,” Dean said, turning in the front seat to wink at Castiel.

“Yeah,” Cas said, “See ya.” 

Castiel quickly got out of the car before either Winchester could see the blush he felt. 

He went upstairs to an empty apartment. He didn’t know where Gabriel was and he didn’t care. He collapsed on his bed and closed his eyes, able to replay the wink enough times to fall asleep with a smile on his face. It was a terrible idea but he couldn’t help liking Dean. His winking and confidence was magnetic. 

 

~~~

 

The following Wednesday, Dean and Benny were standing on their corner conducting business as usual. They were both smoking and Dean kept not so subtly looking over at Castiel’s bench. 

“You missing your weird little friend, brother?” Benny grinned.

“What? No,” Dean said defensively. “And he’s not weird.”

“You called him that first,” Benny argued. 

Truth was, Dean hadn’t seen Castiel since Saturday and he _was_ a little worried. But there was no way he was telling Benny that. It wasn’t worth the teasing and Dean knew he would deserve it. There was no need to worry about someone he barely knew, he had bigger problems. He also didn’t have any way to contact Castiel so they would just have to wait and see. 

“Shut up,” Dean said because Benny was still grinning. Benny laughed as he took a drag of his cigarette. Dean did the same. 

They had relaxed for about a minute before a cop car pulled up and stopped right in front of them.

“Good afternoon, gentlemen,” the officer said across the car through the open passenger window. It was Officer Victor Henriksen of CPD Narcotics, a regular thorn in the sides of Dean and Benny, plus the rest of their crew.

“Henriksen,” Dean said as a greeting. 

“What are you two doing just standing around on such a beautiful day?”

“We’re enjoying it,” Benny smirked, “sir.”

“Just standing around isn’t a crime,” Dean tried, puffing on his cigarette. 

“Actually, it is. It’s called loitering.”

“Touche,” Dean grinned.

“You should know, I’ve picked you up for it before,” Henriksen said. 

“Yeah, and it didn't stick because it was bullshit,” Dean responded, crushing his cigarette boot under his boot.

“Now,” Henriksen said, still from the car, “you boys aren’t doing anything worse than loitering, are you?” 

“No, sir,” Benny said, voice dripping with over the top and fake kindness. He dropped his own cigarette butt on the ground and smashed it under his boot.

“Well, now you’re both littering,” Henriksen said, as he started to get out of his squad car.

“I think we’ve been here long enough,” Benny said quietly with a sideways glance at Dean. 

“Usual?” Dean muttered and Benny nodded.

“What are you two muttering about?” Henriksen demanded to know. 

At that, Dean and Benny both took off running down the sidewalk in opposite directions. 

Dean, without turning around, could hear pounding footsteps and knew Henriksen chose to follow him.

“Shit,” he breathed as he ran. 

As someone who got regular exercise running from the cops, Dean was fast but Henriksen was right on his ass. He turned down an alley and sprinted towards the end where he was met with a wooden fence. Dean quickly climbed up a dumpster and jumped, grabbing the top of the fence and dangled there.

“Get back here, Winchester!” Henriksen shouted as Dean hung, his echoing footsteps getting louder and louder.

Dean pulled himself over the fence as Henriksen got there and jumped, narrowly missing grabbing onto Dean’s foot. 

“Sorry, Vicky, you gotta be quicker than that!” Dean yelled victoriously from the other side of the fence.

“I will catch you Winchester, just you wait!”

“Oh, that I’d love to see!”

Henriksen could hear Dean’s smug laughter as he ran away.

 

~~~

 

The next night, Cas was trying to watch T.V. and relax but Gabriel kept adding his own commentary.

“I just don’t understand this show,” Gabriel complained. “What’s going on?”

“I don’t know, you won’t shut up,” Cas snapped.

“Whoa, what’s with the stick up your ass?” Gabriel responded.

Castiel turned to glare at his brother.

“Just saying,” Gabriel muttered, putting his hands up in surrender.

Cas didn’t mean to snap at Gabriel, the show really didn’t make sense whether Gabriel talked or not, but he had been on edge since Saturday. Henriksen and Mills had failed to mention the rivalry of the gang he was trying to join and the other one. Cas had no idea how dangerous the other guys were and he had the feeling that Mills and Henriksen didn’t know either.

“I’m going out,” Cas said as he got up off the couch. 

“Where?” Gabriel asked.

“Just for a walk,” Castiel answered. He usually went for walks when the apartment got too stuffy or he just needed to clear his head.

“All right,” Gabriel said hesitantly, “be careful.” 

 

Castiel was walking down the street kicking a rock. He hoped he hadn’t gone too far, the streets had kind of all blurred together.

“Cas?” 

Castiel’s head turned. To his left, Dean was leaning against the wall of a building, smoking. 

“Hello Dean,” Castiel said, startled to see Dean.

“What are you doing here, man?” Dean asked with a smile, blowing smoke out of the side of his mouth. 

“I was just walking,” Castiel admitted, “I don’t even know where I am.” 

“You’re at the Roadhouse. Best damn bar in the city,” Dean paused, “At least that I’ve been to anyways.”

“Are you 21?” Castiel asked, tilting his head. He knew from Dean’s police file he wasn’t but he had to ask because Cas remembered he shouldn’t know how old he was. 

“No, only twenty. But I round up,” Dean winked, “and I know the owner, family friend. You should come in!”

“I’m only twenty. Maybe you know the owner but I don’t,” Castiel protested.

“Well, you know me,” Dean smiled. “All the guys are here, if you didn’t meet them at Crowley’s, you can now.”

“I don’t know…”

“Come on, Cas. There’s plenty of hot chicks in there,” Dean stopped, eyeing Castiel for a moment, causing him to shift his weight from foot to foot. “Or guys if that’s what you want.”

“Not that it’s any of your business,” Cas said, taking a normally brazen Dean aback, “but I’m not particular.”

“Huh,” Dean answered, “neither am I.” 

Now it was Cas’s turn to be taken aback. He would not have guessed someone like Dean swung both ways. He had a lot of bravado and over-the-top masculinity but Cas should have known better than to judge anyone based on stereotypes. 

Dean crushed the butt of his cigarette under his boot and opened the door to the bar, letting music, clinking glasses and laughter filter out into the night.

“Shall we?”

Castiel nodded and followed Dean into the bar. 

As the two of them walked in, Dean was explaining how he knew the owner, Ellen Harvelle, and her daughter Jo. 

“I’ve known them for forever. Ellen’s married to Bobby, who’s like an uncle to me and Sam,” Dean said. He put his brown leather jacket on the back of his chair as they sat at a small wooden table with surprisingly comfortable chairs. The bar was dimly lit but big and spacious. “Bobby used to work with our dad and they live in the same building as us.”

“Used to?” Cas asked. Dean didn’t answer, just looked behind Cas, and he just figured he didn’t hear him over the music and other noise. The file Cas saw from the police only said that Dean was Sam’s legal guardian but not why. 

“Winchester, I see you brought your friend around again,” a voice drawled behind Castiel. Crowley had walked up to their table. 

“Yeah. Cas, you remember Crowley.”

“Of course. Great party last weekend,” Castiel managed, trying not to sound lame. 

“Until Michael and his crew showed up,” Crowley paused, lost in thought for a moment. “Glad to see you again, Cas.”

“He’s a little…uh,” Castiel said as Crowley walked away.

Dean just laughed.

“That pretty much describes him.”

It wasn’t long until Crowley’s spot next to the table was taken by Benny who actually sat down. 

“Evening, gents,” Benny said with his slight Southern twang. 

“Hey Benny,” Dean smiled. Castiel nodded his greeting. 

“What are you boys up to tonight?” Benny asked. 

“The usual,” Dean smirked.

“Drinking, hustling pool and looking for hook-ups?” 

“You know me, what else?”

“Can I get you guys anything?” asked a blonde girl who stood next to their table. She said guys but was only focused on Dean.

“Yes you can, Jo,” Dean winked. “How about a round of shots?”

“Be right back,” Jo said, looking down with a smile.

“You should leave her alone, Dean. She’s all over you and you don’t feel the same way,” Benny said.

“Oh, but it’s so much fun,” Dean said with a small smile leaning back in his chair. 

“That’s not very nice,” Cas chimed in, earning a glare from Dean and a nod from Benny. 

“Here you go,” Jo said as she set a tray with three shot glasses on their table.

“Thanks, Jo,” Dean smiled at her as he grabbed a shot glass as did Benny. 

Jo walked away and Dean and Benny looked at Cas expectantly, who still hadn’t picked up the remaining shot glass. Cas was kind of regretting coming into the bar. He had let himself believe, briefly, that Dean wasn’t an asshole but he was wrong. Maybe there wasn’t anything else under the tough guy act like Cas had hoped.

“Come on, Cas, take a shot with us,” Dean goaded. 

“I’d rather not,” Cas replied. 

There was a brief pause before Dean just shrugged and took the third glass for himself.

“More for me,” Dean said, “cheers!” He tapped one of his glasses with Benny’s and they threw them back. Dean did the same with his second shot. Cas assumed Dean had been drinking before Cas even showed up but he seemed fine and Cas wasn’t going to baby him or tell him to stop. Clearly, he did this a lot.

“All right, I’m gonna get a beer and play some pool,” Dean said, getting up and heading to the counter Jo was behind. She smiled as he walked over. On the right side of the bar was a group of about five mean looking guys playing pool.

“He’s going to mess with those guys?” Cas asked Benny. 

“Don’t underestimate him, he can handle it,” Benny laughed.

“So, this is what you guys usually do?”

“Generally, yeah. This or drag racing behind a store we normally hang outside of.”

“Drag racing?” This was news to Castiel who figured Henriksen and Mills didn’t know about it.

“The other gang that crashed the party? We race them.”

“How do you guys do?”

“Pretty good,” Benny laughed, “especially if Dean is racing.”

“Isn't that car kind of old?” Cas asked doubtfully. 

“Whoa, don’t let him hear you talk about his baby that way. He’s the best we got.”

Castiel had to laugh. He watched Dean, who had gotten his beer after he had stopped flirting with Jo, and was headed to the pool table. As Benny and Cas sat there, Benny introduced Castiel to some of their usual crew. He officially met Dick, the bouncer from the party, his close friend Edgar and Jake. There were other guys but Cas forgot their names.

“Well, my girlfriend’s here. I’ll catch you later, Cas.”

Benny got up and headed to the door where Andrea had just walked in. Since Castiel was left alone at the table, he decided to take the tray with the empty shot glasses back up to the bar that Jo was behind.

“Thanks,” Jo said, looking shocked. “Most people in here aren’t very helpful. I’m Jo by the way.”

“Cas,” Castiel said, choosing to stick with the nickname Dean gave him. 

“Can I get you something to drink, Cas?” Jo asked. 

“No thanks. I’m not much of a drinker,” Cas said, taking a seat on a stool across the counter from Jo.

“I’m only 19 so my mom doesn’t let me drink here. It’s her place.”

“Ellen, right?”

“Yeah, how’d you know?”

“Dean told me.”

“That would explain it,” Jo huffed.

“He said he’s known you for a long time.”

“Pretty much as long as I can remember, yeah.”

“So you know Sam, too?”

“Of course. There’s not much I don’t know about Dean,” Jo sighed. She looked at Dean, who was laughing as he played pool, before she kept cleaning glasses.

“So, you know he…”

“Sells pot?” Cas nodded. “Yeah, I buy from him. Don’t tell my mom,” Jo said, casting a worried glance at the door behind her that read “Office.”

“Why? You don’t want to get in trouble or you don’t want Dean to?”

“What do you mean?” Jo glared. Cas threw his hands up in the air defensively. He only just met Jo but he knew he wouldn’t want to get on her bad side. 

She gave up glaring and sighed.

“That obvious?” Jo asked, discouraged. She had stopped washing the glasses.

“Yes. And you only had to come to our table once.”

“Oh God, you’re not a jealous boyfriend or something are you?”

“What? No we’re, uh, friends.” It was weird to use that word describing himself and Dean. They hadn’t known each other long and it was kind of a weird situation. 

Jo let out a breath of relief. 

“Don’t worry about me, I don’t see Dean like that,” Cas assured her. 

“I can’t help it, you know? He kind of rocks the bad boy thing.”

Cas shrugged as Dean walked over to the bar with a wad of cash in his hand and a smirk on his face. Cas wasn’t going to say it out loud but Jo might have had a point even if he was an asshole. Dean was still charming when he wanted to be and Cas didn’t blame Jo for crushing on him.

Dean walked up to Cas at the bar, stood next to him, but turned to talk to Jo across the counter. 

“Hey Jo, I have enough to cover last night’s drinks, the ones I’ve had so far tonight and I’d like a couple more shots,” Dean smirked. Cas could see the alcohol was getting to Dean a little because his cheeks had gotten slightly pink, obvious even in the dimly lit bar. 

He handed some of the money to Jo and put the rest in the back pocket of his jeans. Jo poured two shots of whiskey and pushed them in front of Dean. 

“Sure you don’t want to drink, Cas? My treat. Those guys sucked at pool.”

“I’m all right, thank you. Dean, those guys seem angry.”

“Course they are. I just won all their money!” Dean exclaimed, taking one of the shots.

“No, like really mad. Want to kill you mad,” Cas said, looking uneasily at the scary guys still by the pool table.

“I can beat them in pool and I can beat them in a fight,” Dean said arrogantly, taking the other shot.

“Thanks, Jo,” Dean winked. 

The door behind Jo labeled “Office” opened and a brunette woman walked out. She had a stern but motherly look about her, with brown eyes and a mouth set in a tight line. 

“Jo, take care of the newcomers,” she said. Jo went to the table of four young women that had just come in to take their order.

“Hi, Ellen,” Dean said with a small smile. Cas noticed Dean stood up straighter when talking to Ellen with obvious respect. 

“Don’t you ‘Hi, Ellen’ me, Dean Winchester. You better…”

“I paid, I paid! Ask Jo!” Jo came back to the counter and Ellen did just that. Jo confirmed that Dean had paid off his tab.

“See?” Dean joked. 

“Good,” Ellen responded, “otherwise I would have kicked you out on your ass.”

Dean pulled out money to buy another beer. Ellen got it for him.

“And if any cops ask?” Ellen asked, before handing the beer over.

“I don’t know you or your bar. Come on, Ellen. You know south siders don’t talk to cops.” 

Ellen nodded then turned to talk to Jo so Dean turned to Cas.

“Let’s play pool.” 

“Are you going to take my money?” 

“Why, Cas, I’m offended,” Dean said, feigning offense. Cas just raised his eyebrows. 

“I’d only take your money if we made a bet, win it fair and square,” Dean said, rolling his eyes.

“All right. Well I’m not very good, so let’s keep money out of this,” Cas said. 

The scary guys had left when Ellen had come out of her office and Cas figured they knew she wouldn’t take any crap in her bar.

They played for a while and Dean kicked Cas’s ass at it. After the second game, Dean went to the bar to get another drink. Once he finished flirting with one of the girls from the table of four, he came back for a third game. 

During this game, Cas was doing a little better. He had gotten the hang of it and Dean was getting more drunk as time passed. Benny walked over to the pool table.

“Hey, man. What happened to Andrea?” Dean asked with a slight slur to his words. Cas had been trying to keep track of how much Dean had to drink but it had become impossible. 

“We had an argument,” Benny said glumly.

“Again? I’m sorry,” Dean said. Cas got a hint of boredom in his response and guessed that Benny and Andrea argued a lot. 

The girl Dean had been flirting with walked over towards the pool table, eyes focused on Dean. Cas turned around and didn’t see her friends in the bar anymore. 

She went straight to Dean and whispered something in his ear. He took her hand and led her towards the back of the bar without a backwards glance.

“Is he… are they…” Cas stammered in disbelief. 

“Yup,” Benny said, casually picking up the pool stick Dean was using and sinking the nine ball.

“In the bathroom of a bar?”

“Yup.”

“I’m guessing this isn’t the first time?”

“Far from it, man.”

Cas glanced at the bar. Jo was cleaning, trying to keep busy, but was glaring at the glasses like she wanted to throw them all on the floor. Or at Dean. 

Cas and Benny played some pool and it was a much more even match. 

The bar had started to clear out when Dean finally came back. Cas looked at his watch which read about two in the morning. The girl Dean was with probably snuck out the back which was probably for the best because Jo might have killed her. 

Dean stumbled over to the bar. 

“Hey, Jo,” he grinned, “how about another beer?” He reached into his back pocket but didn’t find any money. 

“How about you get the hell out before my mom sees you like this and kicks you out forever?”

“Ah, come on, Jo.”

Cas and Benny watched the train wreck that was Dean trying to sweet talk Jo into another beer but she wasn’t having any of it. Finally, Cas decided to step in. 

“I’ll get him out of here,” Cas said to Jo. He turned. “You’re going home, Dean.”

He put a hand on Dean’s shoulder to lead him towards the door.

“Thank you,” Jo said. Cas nodded. 

“You need help?” Benny wondered. 

“Uh, do you know where his car is?” Cas asked. 

Benny nodded.

“We’ll take him to it and I can drive. I’m used to taking care of my brother when he’s smashed,” Cas continued. 

“I’m not smashed,” Dean protested weakly. Cas rolled his eyes. 

“Shut up and give me your keys,” Cas demanded.

Dean stuffed a hand into the front pocket of his jeans and handed Cas the keys to the Impala as he steered them towards the door.

“Wow, he really must be out of it to let anyone else drive his baby,” Benny laughed. 

The three guys walked outside and Benny pointed out where Dean’s car was. He made sure Cas could handle the situation and said goodbye, walking away down the street. 

As they got to the Impala, Dean immediately got into the driver’s seat. Luckily, it was an older car with a bench front seat so Dean could move to the passenger side.

“Dean, slide over. You’re not driving,” Cas commanded. Dean silently slid over. Cas carefully climbed in and shut the door. He let out a deep breath before starting the car. 

“Okay,” Cas said quietly. He had just started the Impala and was terrified of hurting Dean’s baby. He couldn’t piss Dean off, he needed to get into the gang to save his own ass. 

As he pulled out onto the thankfully empty street, something dawned on Cas.

“Dean, where do you live?” 

“Oh, we’re going to my place?”

“Yes. You’re drunk and you need to go home and sleep.”

“That’s it?” Dean said suggestively. 

“Yes,” Cas said, shifting a little on the seat. He felt Dean move about an inch closer. 

“Where do you live?” Cas repeated, trying to ignore how close Dean had gotten. It was difficult.

Dean alternated between giving directions and saying things about Cas coming home with him that were making him blush. His pink lips, his ass, his tousled hair he wanted to make messier…

“Stop, Dean,” Cas said. His cheeks were burning and he couldn’t help squirming. 

“Aw, why, Cas? You embarrassed or someth…”

“You can’t even talk and we’ve been driving in circles. Do you have any idea where we are?”

Dean shook his head but was smiling. Cas rolled his eyes. This was ridiculous.

“Give me your phone,” Cas insisted. Dean listened. Cas scrolled through the contacts as they sat at a red light and stopped at the one labeled “Sam.” He dialed as the light turned green and he eased the Impala into the intersection, still being extremely careful. 

“Dean…” a sleepy voice answered. 

“Actually, it’s Cas.”

“Cas? Is Dean okay?” Sam said, suddenly awake. 

“Yeah, he’s fine. Well, drunk, but he’s fine…”

“You think I’m fine,” Dean laughed to himself, trying to lean on Cas who pushed him off. 

“Hush,” Cas said before talking to Sam again. “He doesn’t know where he lives right now.”

Sam sighed and directed Cas to their apartment when he told him the intersection they were at. It would have been a slightly long walk to the Roadhouse but that made more sense than driving when he was going to be drinking. Most people walked in the city but Cas knew how much Dean loved to drive his car. Cas got them home, parked right out front and hung up with Sam. 

“Dean, we’re here. Hold on,” Cas said, walking around the car to help Dean out of the car. 

“So Cas, you’re coming upstairs, right?” Dean mumbled. Cas barely heard him. 

“Well, yeah…” Cas answered, guiding Dean up the front steps of his apartment building. 

“And then you’re staying the night?” Dean asked.

“No, I’m going to hand you over to your brother.”

“You should stay.”

“What? Why?” Cas asked, half dragging Dean towards the elevator. He pressed the “up” button and waited. 

“‘Cause you’re cute, that’s why,” Dean said, completely out of it and looking at the floor. 

“Come on,” Cas said, pulling Dean onto the elevator and pressing 3. He was glad he remembered to ask Sam what floor they were on.

He also chose to ignore Dean’s comment, like he was ignoring the other ones. Or trying to, anyways. Cas dismissed it as a drunk guy who was used to sleeping with anyone he wanted and he told himself that the charm wasn’t working. This seemed to come out of nowhere and Cas really didn't know how to respond to flirting. 

“I’m serious,” Dean slurred. 

“Right,” Cas rolled his eyes, “you just want to get in everyone’s pants.”

“Maybe just yours.”

Cas felt his cheeks redden, again, as the elevator dinged for the third floor. As he pulled Dean towards apartment 3C on their left, he had to ask himself, _How can he still smooth talk when he’s this drunk?_

_He’s drunk, he doesn’t know what he’s saying… or mean it_ , Cas thought, trying to convince himself the flirting wasn’t working. _He just wants an easy lay, like he’s used to…_

Sam must have heard them coming and opened the door to their apartment. Dean looked up and saw his brother.

“SAMMY!” he yelled. Cas immediately clamped a hand over Dean’s mouth and Sam helped drag Dean into the apartment. 

“Jeez, Dean, you’re a mess,” Sam scolded. 

“Sam, this is Cas,” Dean said, “he’s staying the night.” 

“We’ve met before,” Sam rolled his eyes.

“No, I’m not staying,” Castiel insisted, then turned to Sam, “he keeps saying I am.”

“Wouldn’t be the first time he brought some girl or guy home,” Sam sighed. 

“I mean, not that there’s anything wrong with that,” Sam added, seeing Cas’s raised eyebrows, “he just usually wakes me up is all. All right, Dean. Bed time.”

Sam started to lead Dean towards a bedroom to the right of the front door.

“Make Cas stay,” Dean demanded.

“No, Dean, I have to go home,” Cas repeated. 

“Saaaaam,” Dean whined. He began to fight Sam and tried to get out of his grip. The two wrestled for a couple minutes. 

“You could stay, we have the couch,” Sam suggested, giving up.

“I couldn’t, really, it’s fine, I can walk home,” Cas tried.

“Please,” Sam pleaded, “if it will shut him up?”

“All right,” Cas gave in, “Dean, I’m staying on the couch. Now go with your brother.” 

Dean listened and went with Sam into his room. Cas sighed and kicked off his shoes before sitting on the couch. He leaned forward and started to rub his temples. A clock above the TV read quarter to three in the morning. 

Sam must have gotten Dean to go to sleep and walked out of the room, shutting the door behind him.

“I’m sorry about that,” Sam said bashfully, “thanks for getting him home. And staying.”

“You’re welcome, Sam.”

Sam grabbed an extra blanket from a closet to hand to Cas before saying goodnight and disappearing into the bedroom a few feet behind the couch. Castiel put the Impala’s keys and his now dead cell phone on the coffee table and turned off the lamp next to the couch. 

He lay down and got comfortable but it took longer than he hoped to fall asleep. Cas couldn’t help but think about Dean’s flirting and how close he was to him right now and that he was staying in his apartment… 

_No_ , Cas told himself, _that’s not happening. Forget it._

 

Cas woke up when the door behind the arm of the couch opened. He propped himself up on his elbow and saw Dean standing in the door way of his room.

Dean was rubbing sleep out of his eyes when he saw Cas on the couch and paused. He was still wearing his clothes from last night, a black T-shirt and jeans. His leather jacket must have been in his room somewhere. 

“Ugh,” Dean groaned, “it wasn’t just a bad dream. Morning, Cas.”

“Hello Dean,” Cas said, sitting up on the couch. 

“I…” Dean started to say. His hand flew up to cover his mouth and he ran to the bathroom. Cas could hear him throw up violently. 

Cas was about to go check on him when Sam opened his bedroom door that was next to the bathroom, both behind the back of the couch, and shuffled out. Sam’s floppy hair that was down to the ends of his ears was messy and he wore a big gray T-shirt and red plaid pajama pants. He appeared to be moving on auto-pilot and Cas wondered how many times he had woken up to take care of a hungover Dean. 

After an awkward few minutes for Cas, Sam walked out of the bathroom, said hello to Cas and went into the kitchen. Cas smelled bacon cooking and heard Dean brushing his teeth. 

Cas checked the clock above the TV and saw it was seven in the morning. Since it was Friday, he could only guess that Sam had school.

When Dean finished in the bathroom, he and Cas waited at the tiny kitchen table for Sam to finish cooking. Cas saw he was making eggs as well.

“Cas, I…uh,” Dean began, rubbing the back of his neck, “I didn’t do anything embarrassing last night, did I?”

Castiel thought of the girl he disappeared with and the shameless flirting he did with Jo and then him. If Dean didn’t remember what he said than it really didn’t matter all the flirting he did. It must have been automatic for him after he drank.

“No,” Cas lied. Sam placed the food down on the table along with orange juice.

“Eat up,” he ordered Dean as he sat down.

“Thanks,” Dean mumbled.

“You’re welcome,” Sam said, munching on bacon. 

“I should go,” Cas said, not wanting to intrude any more. Dean started to protest, saying he should stay and eat as thanks for taking care of him but Cas said his own brother would be worried. 

“All right,” Dean gave in, “do you want a ride?” 

As he said that, his eyes got huge and he dropped his forkful of eggs. 

“My car!”

“Dean, it’s fine,” Cas reassured him, “I drove us here last night.”

“You drove my car?” Dean said. Cas wasn’t sure if he was mad or not, it was hard to read his expression. 

“Yeah,” Cas said slowly. He saw Sam had wide eyes and his glass of orange juice paused halfway to his lips. 

Dean nodded and continued to eat his eggs. 

“I guess that’s good. I was clearly in no shape to drive yesterday,” Dean said with a mouthful of eggs, “She made it home okay?”

“Yes, not a scratch. I parked right out front,” Cas smiled. Dean smiled back and Sam let out a sigh of relief. 

“I really should go,” Cas said reluctantly. He hadn’t even eaten anything. He stood and headed to the front door. Dean got up to follow him.

“Hey, Benny and I had to move. Trouble with the cops,” Dean said quietly, casting a wary glance at Sam. “Let me get your number and I can text you our new spot.”

Cas managed to give Dean his number without turning red or stumbling, which he was thankful for. 

_Why that would be a big deal, it’s not, it’s just your number_ … Cas mentally kicked himself. 

“I’ll text you after I go back to sleep for a while,” Dean grinned. From the table, Sam coughed.

“I have to, uh, get ready for school,” Sam said, heading back into his room. 

“Well, I’ll see you later then,” Dean said.

“Bye, Dean,” Cas said, heading down the hallway. Dean shut the door behind him then sat on the couch, picking up his keys.

“Son of a bitch drove my car,” Dean laughed to himself. 

There was a vague recollection of Cas driving and he didn’t mind. Normally, he’d be furious if someone other than him or Sam drove the Impala. Hell, he barely let Sam drive it. 

But something about Cas…

Sam opened his bedroom door, interrupting Dean thinking about Castiel and his car.

“Dean,” Sam started. 

“Not now, Sam,” Dean said, getting up off the couch to head to his room for much needed sleep.

“I was just saying, it’s not like you to forget a lot of stuff when you drink. I’m worried,” Sam said. They were on opposite sides of the couch now.

“I remember pretty much everything,” Dean said with an air of finality that Sam ignored. “Just not really how we got here, that’s a little blurry. I mostly know what I said though.”

“What? Then why did you pretend you didn’t?” Sam asked, confusion obvious with his furrowed brow. 

Dean sighed and turned to go into his room. 

“Dean, come on. Don’t do that.”

“Do what?”

“Walk away. Just talk to me, man.”

Dean looked at the pleading look on his younger brother’s face and had to give in.

“Fine,” Dean said, sitting on the couch. Sam joined him.

“Why’d you lie?” Sam asked bluntly. 

“I said some embarrassing stuff to Cas so I was pretending it didn’t happen. I thought it would be better.”

“Like what?”

Dean didn’t say anything. 

“Dean, I’m your brother. You can tell me anything.”

“Fine,” Dean said, slightly snapping and figuring he was going to regret this. 

“I, uh…” Dean stammered, looking at his hands, “I remember I kept hitting on Cas.”

Sam started laughing hysterically and Dean stood up abruptly. 

“This is why I don’t tell you anything!”

“I, but… really?” Sam said, struggling through his fit of laughter. “I mean, just the way you two were looking at each other this morning…”

Dean crossed his arms to add to an intense glare.

“You done?”

Sam attempted to turn his laugh into a cough.

“Yeah, yeah,” Sam smiled, “but why ignore it and lie?”

“I think pretending it didn’t happen will be better. We can just be friends. That would be easier.”

Sam tried not to keep laughing but he couldn’t help it. 

“Go to school, Sam,” Dean said, throwing the car keys to Sam.

Sam raised his eyebrows and Dean nodded.

“You’re a good brother even if you’re a pain in my ass,” Dean said, turning to go into his room for a little bit of sleep. 

“Thanks, Dean,” Sam said before leaving their apartment. 

Dean fell back onto his bed. He tried not to think of Cas and his messy hair… blue eyes… what he kind of remembered of how he responded to his flirting, getting all flustered, and how he must have looked driving the Impala…

He did try to stop but not successfully. Even if Dean was going to try to pretend it didn’t happen later, he could picture Cas blushing at what he said for a while.


	3. Chapter 3

Castiel walked home from Dean’s and thought about what happened the night before. He figured if Dean didn’t remember all of his flirting than he didn’t mean any of it, either. That was probably how he always acted when he was drunk, just flirted with anyone trying to get laid. 

_Just forget it and move on_ , Cas thought. It would be stupid to bother with Dean in that way. Cas decided he would just do his job for the cops and shut down Dean if he tried anything else. It was for the best.

_The sooner I do my job, the sooner everything goes back to normal._

Cas walked through his apartment’s front door and was immediately ambushed into a very tight, engulfing hug. It was like being attacked by a python and it was hard to breathe. 

“CASTIEL!” was yelled into his ear by none other than his older brother.

He couldn’t answer without air and Gabriel let go of him but stayed in his face. Cas breathed in a large gulp of air.

“Where the hell have you been? I texted and called for hours, I didn’t sleep, I almost called the cops! Fuck, you can’t just ‘go for a walk’ and disappear! I thought you were dead in a gutter.”

Cas dug his phone out of his pocket and showed Gabriel it had died.

“My phone died?” Cas’s excuse came out like a question. 

He knew it was lame. Honestly, he forgot to text or call Gabriel since he had been with Dean but that excuse wouldn’t make his brother feel better. It didn’t make Cas feel better either, he didn’t think Gabriel would panic like this.

He walked around Gabriel to get into the apartment. 

“Your… your phone? Died?” Gabriel seethed. Cas turned around and jumped when Gabriel slammed the front door. 

“I’m sorry…” Cas said, backing away step by step. 

Gabriel charged towards Castiel, yelling that he would kill him for making him worry. 

Cas ran around their table and then their couch before dashing safely into his room and slamming his door. 

“CASTIEL!” Gabriel banged.

“No, go away.”

“Let me talk to you.”

“No thanks, you just threatened to kill me. I’m all right in here.”

“Fine. I’ll talk through the door,” Gabriel reasoned. “You can’t do that to me, I seriously thought something happened to you.”

“I’m sorry,” Cas replied sincerely. 

“You’re all I got. I can’t lose you.”

“I know. I’m sorry.” 

“I’m glad you’re okay,” Gabriel said.

For so long they only had each other and Cas would have been just as upset if this was the other way around. Maybe they didn’t always get along but he was the only person Cas could always count on. 

They stood on opposite sides of the door in silence until Cas heard Gabriel head to his own room. 

 

Cas spent a good three hours in his room, dozing in and out, until his now charged phone buzzed. He didn’t recognize the number.

 **Hey meet me and Benny in an hour** , the text read.

 **Hello to you too, Dean. Where?** Cas answered right away. He wasn’t worried about taking longer to respond because friends texted back right away.

**2 blocks south of the usual**

**Okay.**

Cas spent the next hour mentally preparing himself. It would take everything he had to ignore Dean if he decided to keep flirting like he did last night. Everything Dean said made Cas blush and his stomach flutter a little. Cas tried to convince himself he was just lonely and would have appreciated attention from anyone but he knew that was a lie since he rarely felt like this about anyone. Of course he had to have a stupid crush on the last person he should possibly think about like that. It would be in his own best interest to move on. The threat from the police of going to jail for stealing a car if he didn’t do his job here should have been enough motivation to forget about Dean.

 _Just get in the gang, get enough information and you’re done and you can forget about Dean_ , he told himself. 

The more rational part of his brain knew he didn’t want to forget Dean but he decided to ignore that part. What the hell did it know?

 

When Cas showed up at the new location, Dean stood alone against the wall of the corner store in a red plaid shirt and jeans, already smoking. His light brown hair was spiked in the front a bit. The awning of the corner store was providing a little bit of shade out of the summer heat casting a shadow over Dean.

 _He looks good, maybe Jo had a point about the whole ‘bad boy’ thing…_ Cas thought. He quickly shook that out of his mind as he walked up to Dean. He really had to focus.

“Hey Cas,” Dean paused to inhale, “how ya doin’?”

“I’m fine. How are you? You had a rough night. And morning.”

Dean cringed. 

“Yeah, that wasn’t my finest evening. Sorry you had to see that, I know I was difficult when you finally got me home.”

“I thought you didn’t really remember last night?” Cas said, squinting and tilting his head in confusion.

“Oh, I, uh… don’t. Sam helped to fill in some blanks.” 

Castiel nodded and leaned against the wall next to Dean.

“So,” Dean said, rubbing the back of his next, “Benny couldn’t make it but I, uh, decided something. I can trust you. I mean, after last night… not many people I hang with would help me like you did, you know?”

Cas didn’t say anything. It sounded like maybe Dean needed to keep better company. Dean took a drag of his cigarette. 

“I’m going to sell to you, Cas.”

“Oh. Thanks, I guess.”

Cas pulled the twenty out of his pocket that he had been holding onto from the cops to finally buy from Dean. 

“Whoa, whoa, whoa. Subtle, man. Like a handshake,” Dean said, using his non-smoking hand to make the transaction. 

Cas put the baggie of weed into his pocket.

“Maybe you can help us to sell even. I could talk to Crowley,” Dean suggested.

This was it. Castiel was getting in.

“Uh sure. You know, I’ve never really done this before,” Cas admitted.

Dean laughed.

“Then why the hell would you want to?” Dean asked. “Meg was right, you do seem a little too good for this. More of a bookworm look about you then drug dealer.”

“I don’t know,” Cas lied. “Bored, I guess?”

Dean laughed again.

“Why do you do this, Dean?” Cas asked, genuinely curious. Dean didn’t seem like the drug dealer type either, not to Cas.

“I don’t have a choice,” Dean said, looking away. 

“Why don’t you have a choice?” Cas asked.

“Long story, man,” Dean answered .

There was a pause. Cas didn’t want to pry so he shifted gears.

“What happened with the cops to make you move?”

“Henriksen, this cop, tried to bust me and Benny a couple of days ago. We got away and decided to come here instead.”

“I met Henriksen, the night of Crowley’s party.”

Dean nodded. 

“Right. He’s a pain in the ass,” Dean said, putting his cigarette out under his boot.

“Where is Benny?” Cas asked after a pause. It felt a little weird to be hanging on the street corner without him. 

“Got called in to the diner where he works last minute,” Dean answered, lighting up another cigarette.

“Should I… go?” Cas asked. He was unsure because he finally bought and didn’t know if Dean would want him to stay now. 

Dean thought about it as he inhaled. He then took his time blowing smoke out of his mouth, away from Cas.

“Nah,” Dean said, turning his head to look at Cas, “you can stay if you want.”

Cas let out a small sigh of relief and smiled. Despite what he tried to tell himself earlier, he wanted to spend time with Dean, even just as friends. He hadn’t really hung out with anyone this much outside of Gabriel in a while. 

It was harmless, right? 

Dean and Cas stood at the intersection for a couple of hours. Whenever Dean made a sale, Cas stood by and tried not to be too awkward. 

A cop car drove by at one point and Cas relaxed only when Dean breathed a sigh of relief because it wasn’t Henriksen and they didn’t stop.

“All right,” Dean said, “I’m all out.”

“Oh,” Cas said, sounding disappointed. 

“That doesn’t mean we have to go our separate ways,” Dean laughed gently at Cas’s clear look of disappointment, “ are you hungry?”

Cas smiled, glad Dean suggested it.

“Where did you have in mind?”

“We could visit Benny at work,” Dean suggested with a shrug.

“That sounds like fun,” Cas agreed.

“Sounds good. Let me just run inside here and we can go.”

Dean walked into the corner store they were in front of and came back a few minutes later holding a new pack of Marlboros. 

He ripped the plastic off the cigarette pack and threw it on the ground as they walked.

“That’s littering,” Cas said matter-of-factly.

“Oh no, call the cops,” Dean rolled his eyes as he lit a cigarette. He put the pack and his lighter back into his jeans pocket. 

“Aren’t you scared of getting arrested?” Cas asked, knowing from experience it sucked.

“Nah,” Dean said, blowing smoke out into the hot June day, “they can’t catch me.”

Cas figured Dean knew he meant arrested for selling weed, not littering, and still wasn’t fazed. He didn’t have a response to Dean’s arrogant reply but he did feel a slight twinge of guilt because he was playing a role in trying to get Dean arrested. 

Cas followed Dean into the small diner that Benny worked at. There were rows of booths along the wall and stools at the counter and an old-fashioned jukebox in the corner. The two sat themselves, waving at Benny who was working the grill in back.

Before they could order anything, Cas excused himself and went to the bathroom. Once inside the bathroom, he called Officer Mills.

“Castiel, what’s up?” she answered, “We haven’t heard from you in a while.”

“Sorry about that,” he replied. 

After the incident with the other gang, he didn’t really want to talk to either officer but he couldn’t blow them off forever. They had a deal.

“Everything okay?”

“Yeah, everything’s great,” Cas said, leaving the part out where he maybe had a crush on one of his targets. He didn’t think Mills would appreciate that.

“Henriksen hasn’t seen Dean and Benny in their usual spot.”

“They moved, two blocks south. I was with Dean there today, he sold to me. And others.”

“Come to the station later and we’ll talk, okay? I have to go but thanks Castiel,” Mills said, hanging up.

Cas left the bathroom and rejoined Dean at their booth. 

“I waited to order,” Dean grinned.

“Thanks,” Cas said, trying not to grin but he couldn’t help it. Dean’s grin was contagious. 

A waitress named Elizabeth came to take their order. Cas copied Dean’s order, a burger with fries. 

“So, Cas,” Dean started, resting his elbows on the table, “I feel like I don’t know much about you.”

“I feel like I don’t know that much about you either,” Cas said, trying to spin it around. 

“You’ve seen me shitfaced, met most of who I consider family and have driven my car. That’s more than I have on you.”

“All right,” Cas sighed, “what do you wanna know?”

“Geez, you make this sound fucking terrible! I’m just making conversation, being friendly,” Dean said with a laugh. 

The way he said friendly, with a pause before it, made it seem anything but.

Cas smiled like he tended to do when Dean laughed.

“Fine,” Cas said good-naturedly, “I live with my older brother and I work at the community college.”

“Really? Doing what?”

“I work in the library but because it’s summer, I don’t get many hours. Which is way I came to you guys, I guess,” Cas said, adding the lie to explain why he showed up at their corner about a week and a half ago. 

“I knew you have a bookworm look,” Dean said, pleased with himself.

“You’re saying I’m a nerd?” Cas asked.

“Maybe,” Dean replied. “Do you go there, too? The college?”

“Uh, no,” Cas said, not caring to elaborate and taking a sip of water. “What do you do, Dean?”

“Besides sell pot?” Dean smirked.

Cas nodded.

“I’m a mechanic, a damn good one. I work in Bobby’s garage, you should meet him.”

Cas agreed that he should. As he did that, Elizabeth returned with their food. 

“You mentioned before your dad used to work with Bobby?”

“Yeah, used to,” Dean said, picking up his burger and looking at it with awe. He closed his eyes as he bit and chewed. 

“What happened?” Cas asked, taking a bit of his own burger. He thought Dean was overreacting but it was actually a very good burger. 

“He died, drank himself to death on Christmas when I was seventeen, senior in high school. I dropped out with one semester left to work for Bobby full time. I became Sam’s legal guardian when I turned eighteen that January,” he paused to take another bite. “Not many people know that.”`

“Your secret is safe with me. I rarely talk about my family.” 

“Anyone besides your brother?”

“No,” Cas responded, biting his burger. Dean took a fry, dragged it through some ketchup and bit it, his eyes not leaving Cas. It was oddly suggestive but so were a lot of things that Dean did because that’s how he was.

“Come on, I just told you my life story…”

“That wasn’t your life story,”

“You know what I mean.”

“Sorry, it’s just… I usually never tell people this. Ever.”

“Your secrets are safe with me,” Dean said, using Cas’s words which made him feel comfortable enough to share.

“My parents died when we were young. We bounced from foster care to group home and everything else. Nothing really lasted, it was always too much to handle two boys, especially when one is my brother. He’s a piece of work.”

Dean laughed at that.

“I should meet him, I’ve been told I’m a piece of work myself,” Dean beamed, “Teachers were always pleasantly surprised to have Sammy after being stuck with me.”

“I bet,” Cas retorted. Dean stuck his tongue out in response. 

“Real mature, Dean,” Cas joked. 

Dean just kept his tongue out as Cas rolled his eyes. A second later, Dean leaned forward. He was completely serious now.

“I don’t even know your last name. Mine’s Winchester.”

“Novak,” Cas smiled. 

“Castiel Novak,” Dean said. 

Cas felt a thrill go through him as Dean said his full name. He mentally kicked himself right after and told himself to pull it together. There was no need to get all gooey just because he liked hearing his name pass through Dean’s lips. 

As they finished eating, they continued talking and laughing. Dean told him about the drag racing Benny mentioned before at the Roadhouse and that it was going on tomorrow night. Cas said it seemed dangerous.

“That’s what it makes it fun,” Dean winked. 

Cas looked down at his empty plate, feeling his cheeks get warm. How stupid was it that Dean could make him blush so easily?

Dean’s foot brushed his under the table, making them both jump.

“You have to try their pie, Cas,” Dean said after clearing his throat. “I’m going to take a quick smoke break, digest a little and then we’ll get some, okay?”

Cas nodded, his brain still a little fuzzy. 

Cas briefly checked his phone. There was nothing from Gabriel or either police officer. When he looked up, Benny was sliding into the booth across from Cas.

“Hi, Benny,” Cas greeted, “on a break?”

“A brief one. How you been?”

“Good. Dean told me about your new spot and we worked there for a while.”

“Worked a new corner? Today?” Benny seemed confused.

“Yeah, he said you had to move spots and you got called into work last minute. I went and then stayed to help. Well, I just stood there, really…”

“Dean knows I work on Fridays. Have for a while now.”

Cas couldn’t figure out why Dean would lie. Benny said goodbye only because Elizabeth was holding a stack of orders for him. He left and Cas waited for Dean to come back in. 

When Dean walked back into the diner he was carrying his red plaid shirt instead of wearing it over his plain white t-shirt. The shirt outlined his arm muscles very well and Cas was staring until Dean snapped him back. 

“Yo, Cas, anyone home?” Dean asked. “McFly?” 

Cas squinted his eyes and tilted his head. 

“You don’t get my _Back to the Future_ reference but you got when Meg called you Clarence?” Dean asked, shocked. 

“My brother likes Christmas a lot, I’ve seen that movie plenty of times and I haven’t seen _Back to the Future_.” 

Dean just shook his head like Cas was a puzzle he couldn’t figure out.

“How are you wearing jeans, it’s too hot out,” Cas changed the subject.

“That’s why I took off the top layer,” Dean explained, gesturing to the button-up next to him on his side of the booth. 

“Why not just a t-shirt and shorts?” Cas said, looking down at his own red t-shirt and black basketball shorts that used to be Gabriel’s. 

“Oh, sweetheart, I don’t do shorts,” Dean winked. 

Cas was giving him a look and was going to say something but it went unnoticed by Dean whose attention was on Elizabeth who had returned to their table.

“I’m guessing you’d like some pie, Dean,” she speculated with a smile.

“I really do come here too much, don’t I?” 

“Not nearly enough,” Elizabeth kept smiling, getting a grin from Dean.

Cas crossed his arms over his chest.

“How about a slice of pecan then?” Dean requested.

“Sorry, Dean. ‘Fraid we’re all out of pecan,” Elizabeth said, her smile faltering a little. 

“Damn it,” Dean cursed, “everytime. All right, apple then. Cas, how about you?”

Dean turned to look at Cas. 

“Cherry, please,” Cas ordered. Elizabeth left to get the pie. 

Cas tried to avoid looking at Dean.

“What’s wrong?” Dean asked. Cas sighed.

“It’s nothing,” Cas replied. 

He didn’t know how to voice his frustration without sounding overdramatic since it really was nothing.

Elizabeth returned with the pie slices from the display on the counter. Dean shrugged at Cas and immediately dug in, closing his eyes as he chewed like he did with the burger.

“Dean, what is this?” Cas asked, not touching his pie yet. His arms were still crossed and his eyes fixed on Dean.

“Heaven,” Dean moaned, mouth full of pie and his eyes still closed. 

“I’m serious,” Cas said, trying not to focus on Dean’s moan and moving mouth, which was very difficult.

“So am I,” Dean said, chewing blissfully. 

“Dean.” 

At Cas’s urgent tone, Dean opened his eyes and swallowed. 

“What is this?” Cas asked again, finally able to look Dean in the eye.

Dean looked from Cas, down to Cas’s untouched slice of cherry pie and back to Cas.

“I call it dessert, Cas.”

“That’s not what I meant,” Cas said quietly, finally taking a bite of his pie. Dean took a small, second bite.

“Then what do you mean?” Dean asked when he finished that bite.

“I mean this, us. What’s going on?”

“Two friends having lunch… or dinner, depending on how you want to look at it,” Dean said, glancing at the clock over the door of the diner. 

“Not everything’s a joke, Dean. Can we just talk for a second?”

Dean took another bite. 

“I’m not usually the type to talk about this either, but…” Cas said.

“Then why talk about it?” Dean suggested as he ate.

“Because… you can’t just flirt with Jo and Elizabeth…”

“Whoa, Cas, what’s the big deal?” Dean exclaimed, taken aback.

“It’s not, not really… but… You can’t flirt with everyone and me too, okay?”

“What do you mean?” Dean’s eyes narrowed.

“Benny told me you know he works Fridays.”

“So?” Dean asked, finishing his last bite of pie. 

“So why bother with just me, taking me here?”

“To get to know you!” Dean refuted.

“You’re looking to get laid, just like last night and like always.”

“Last night… come on, last night I was drunk,” Dean argued, “With Jo, that girl, you.... it doesn’t count!”

Cas opened his mouth then closed it and narrowed his eyes in realization. 

“I thought you didn’t remember last night.”

“I, uh… shit. Look, Cas, I just thought it would be better to forget it.”

“Well, maybe I can’t forget it. Maybe I didn’t mind you flirting with me but then it doesn’t mean anything when you do it with everybody.”

“That’s not fair…”

“No, it’s not fair for you to lead everyone on. Let me guess, you’re not very into relationships, right?”

Dean didn’t say anything so Cas kept going.

“Just one night stands? No commitments, no strings…”

“You’re wrong,” Dean said quietly, “I was in a relationship, it ended a couple months ago.”

“Did it only last a couple months too, maybe just a couple weeks?” Cas snapped.

“No, a year.”

“A… a year?” Cas felt sick. He couldn’t have been more wrong.

“Yeah, a year.”

“I… I didn’t know. Dean…”

“You just assumed,” Dean said, getting angry, “because you don’t know anything about me.”

“That’s fine by me,” Cas said, standing up. He threw some money on the table and marched out of the diner. 

 

Cas stormed to the police station to talk to Officer Jody Mills. He thought Dean was going to follow him out of the diner but he didn’t.

The argument was stupid and they both were at fault for different things but how could Dean blame Cas for thinking he never took relationships seriously, after what he had seen so far? Dean flirted with anyone and everyone.

_A year, Cas thought, holy shit, that’s a long time…_

He finally got to the station and quickly found Officer Mills. 

“Hi, sorry I was so abrupt earlier. We had a lot going on. What do you got for us?” she said.

Cas handed her the weed and gave her an update on selling with Dean and repeated the new location two blocks south of the old location. 

He also decided to mention the drag racing that was going to be happening tomorrow night.

“Really?” Mills asked.

“I guess, they race the other gang, the one that crashed Crowley’s party.”

“Huh.”

“Do you guys know anything more about the other group?”

“No. I’m sorry, Castiel. If we do, I’ll tell you.”

Cas nodded his thanks and showed himself out. 

 

Castiel, after the police station, was feeling particularly on edge as he got home.

The apartment smelled wonderful which meant Gabe was cooking. 

“You hungry?” 

“No, already ate,” Cas answered as he shut the front door behind him. 

Gabriel checked his watch as he stirred what was in the pot on the stove. 

“It’s only five!”

“Yeah, well, I ate,” Cas said, flopping on his back on the couch.

“Everything okay?” Gabriel asked, picking up on Cas’s dejected body language. 

“Everything’s fine,” Cas lied. 

Gabriel resumed cooking with a small shake of his head. 

~~~

The situation was a little different at the Winchesters’ place. Dean opened and closed the front door and got two steps into the apartment when Sam asked him what was wrong. He didn’t even look up from his homework and books scattered around the table. 

Dean sighed and sat at the table with Sam. 

“It didn’t go well with Cas. He found out I lied about last night.”

“I’m shocked,” Sam said genuinely. 

“That it didn’t go well?” Dean asked, raising his eyebrows.

“No, that you’re being honest with me and I don’t have to wring this out of you.”

“Shut up,” Dean said with a halfhearted smile. 

“What else happened?”

“He says I flirt with everybody.”

“You _do_ flirt with everybody, Dean,” Sam pointed out.

“Well, he said he doesn’t like it.”

“Oh.”

“Oh?” Dean asked, confused. 

“If he’s pissed you flirt with other people, he likes you.”

“Really?”

“Really. You’re bad at this, you’re lucky you have me.”

“Right. How’s it going with Jessica again?” Dean tried turning the tables.

“We’re studying together tomorrow,” Sam beamed, “just the two of us.”

“You should take her on a real date,” Dean grumbled, having lost this battle. 

Sam laughed and Dean stood up.

“Keep studying, nerd. I’ll fix you something to eat.”

 

~~~

 

Cas worked for a few hours the following morning, having one thing on his mind.

Dean’s race that night.

Castiel couldn’t figure out if he should go or not and wrestled with it the whole day before deciding he would.

Dean was in a similar situation, nervous about the race and if Cas would show up. He even texted Cas to ask if he was coming, but didn’t get a response. 

The races started at nine sharp. It had gotten dark and was still pretty warm out, but getting cooler. 

Most people were standing around the alley either holding a beer, smoking or both. The guys from both gangs were there but keeping a safe distance from each other. 

The first race of the night was Crowley and Michael but it wasn’t much of a contest. Michael won easily and the two almost got into a fight after but were pulled apart.

Everyone resumed just standing around as Cas showed up. Dean was leaning on the hood of his Impala, smoking, when he saw him out of the corner of his eye. 

It took Dean by surprise how good Cas looked. He wore just a black T-shirt and jeans and Dean coughed as he inhaled. 

“You all right, brother?” Benny asked, smiling as he joined Dean by the Impala. 

“Fine,” Dean wheezed.

“Enjoying the view?” Benny asked, looking at Cas. Dean looked over again. Cas had started talking to Meg. 

“Shut up,” Dean snapped, continuing to smoke. 

Benny laughed and went over to join Cas and Meg, saying hi to Meg and shaking Cas’s hand. Benny was the only guy in the group who knew Dean was bisexual and would always give him a hard time like only a best friend could.

One of the guys from the other gang was disappearing into an alley with a girl which made Dean laugh a little. Considering how things were with him and Cas, he almost wanted to try something like that himself to help him forget. 

Dean stepped on the butt of his cigarette as two of Michael’s guys approached Cas, Benny and Meg. He walked up as Meg left to stand in front of Cas and Benny, making him face to face with Raphael and Zachariah. 

“Oh look, you guys brought fresh meat,” Zachariah taunted, sizing Cas up. Cas didn’t seem fazed. 

“You drive?” Raphael asked, getting to the point.

“No, but Dean does,” Cas responded. 

“We know _he_ does,” Zachariah sneered.

“You also know he kicks your ass,” Benny added. Dean grinned smugly. The people standing around the alley from the rival sides had started to circle up and watch. 

“Zac and I want to see what you’re made of,” Raphael jeered at Cas.

“Can’t help you, I don’t have a car,” Cas said, turning to walk away. Raphael grabbed his right shoulder and spun him back around and left his hand there.

“You don’t want to do that,” Cas growled. 

Raphael was no joke and it took guts to stand up to him. Dean was actually impressed, Cas was kind of intimidating when he wanted to be. It was also kind of hot but that wasn’t the point.

Raphael glared but didn’t move his hand so Castiel pushed it off for him with his left hand.

That was all the provocation Raphael needed and he shoved Cas in the chest with both hands, hard. It sent Cas back three steps who immediately came back with a shove to Raphael’s chest, harder. Dean and Benny moved to intervene but Cas snapped at them to back off.

The first punch was thrown by Raphael but Cas dodged it and retaliated with a solid right hook that hit Raphael square in the jaw. He fell to the ground.

Dean and Benny held Cas back as Zachariah helped Raphael up.

“This isn’t over, someday you’ll pay for this,” Raphael said, standing and holding his face.

“Maybe. But today, you’re my little bitch,” Cas returned. 

As the gangs wandered apart again, Crowley came up.

“You’re definitely tougher than you look, I’ll give you that,” he said. 

Cas acknowledged the compliment with a short nod.

“Nice hit, Clarence,” Meg winked and Cas smiled. 

At that, Dean called Cas over by his car. He was leaning on it and smoking again in his olive green Henley shirt, sleeves pushed up, and jeans. 

“So that’s not flirting?” Dean accused, smoking and not caring if the smoke went towards Cas.

“Why, you jealous?” Cas replied, intrigued by how the tables had turned.

“Damn, one fight and you think you’re hot shit,” Dean laughed. “You even have crappy one liners. His little bitch?”

Cas shrugged and leaned on the Impala next to Dean. 

“I mean… it wasn’t really…”

“Joke, Cas. I was joking.”

“Oh, right…” Cas said, looking down.

“Why don’t we hang out after this and talk?” Dean suggested. 

“I don’t think that’s a good idea, Dean.”

“Why not?”

Cas could think of several reasons why not but kept his mouth shut.

“Come on, Cas. I can’t be that bad.”

Cas smiled just a little. Of course he wasn’t, he was the opposite, and that was the problem.

Cas was going to protest when he saw Michael walking towards them. Dean put out his cigarette and crossed his arms. 

“What?” was Dean’s simple demand. 

“Uriel wants to race you,” Michael said coolly, crossing his own arms. 

“Can he even see straight? Pretty sure I punched him pretty hard last week,” Dean smirked.

“That’s why he’s challenging you.”

“Why isn’t the bastard doing it himself, errand boy?” Dean mocked.

Michael tensed at that, which Dean hoped he would.

“He’s already in his car,” Michael answered, fighting to stay level, “he figured you’d say yes.”

“He’s right, let’s fucking go!” Dean exclaimed, turning towards his car.

Before he got in, he whistled to call his guys, and Meg and Ruby, over. He let them know he was racing Uriel and got a loud cheer in response. 

“Place your bets now boys and girls and I’ll win you some money,” he boasted. 

They dispersed to get ready to watch.

“Be careful, Dean,” Cas said as Dean got into the Impala. 

“Me? You just started a fight, man!”

“I’m serious.”

“All right, all right. I have a bet for you.”

“What is it?” Cas wondered. 

“I win, we talk. Got it?”

Cas thought about it for a second before giving in and shaking Dean’s hand through the window of the car. 

“Wish me luck,” Dean winked. He blasted “Back in Black” and drove up the alley to meet Uriel at the start. They were going to race down to where Cas and everyone was standing and waiting.

Cas mentally kicked himself as Dean drove over. He knew it was a bad idea to spend any more time with Dean than was necessary for his undercover job. On the walk over from his apartment to the race, he told himself to avoid Dean.

How could he though? Dean was hard to ignore.

The race started and was over almost as soon as it began. Despite Uriel being in a newer looking Camaro, Dean kicked his ass. There wasn’t much time for celebrating because police sirens could be heard closing in fast. Everyone dropped what they were doing and ran or drove away.

“Get in!” Dean yelled through the passenger side window, pulling up next to Cas.

He didn’t argue and climbed in. Dean stepped on it and they were gone. 

They didn’t drive far from the race before stopping at what looked like a crappy elementary school with a playground in even worse condition. The whole place looked run down and slightly creepy.

Dean parked the Impala on the blacktop between the school building and playground instead of the parking lot.

“I don’t think you can park here, Dean.”

Dean just laughed and got out of the car. Cas sat and just looked at the sad state of the place where they were for a moment before Dean asked him if he was coming.

Cas, against his better judgment, got out of the car. He joined Dean who was sitting on the hood of the Impala, using the windshield as a backrest. Cas was extremely careful as he climbed up to join Dean.

“What did you want to talk about Dean?” Cas asked. He was all too aware of how close he was to Dean at the moment. Their legs and shoulders were inches apart.

“How come you didn’t answer my text earlier?” Dean questioned with curiosity.

“I didn’t know if I was coming or not,” Cas said, looking at his hands in his lap.

“You could have said that.”

“I’m sorry,” Cas said, looking up at Dean who met his gaze.

“It’s cool, man,” Dean replied, “forget it.”

The two sat in comfortable silence, looking up. There was maybe a single star to be seen because of all of Chicago’s light and air pollution but it was still nice to enjoy the summer night. 

“Dean,” Cas spoke up as he wondered about something, “we talked about your dad, and you don’t have to answer if you don’t want to but…”

“What about my mom?” Dean guessed, looking at Cas again.

Cas nodded. Dean was quick on reading Cas.

“She died when I was four in a house fire. That’s why we moved into our shithole apartment.”

“Was the house in Chicago, too?”

“Yeah,” Dean responded, “They moved here after they got married. My mom’s parents didn’t like my dad so they ran away.”

“Where were they from originally?”

“Lawrence, Kansas.”

“Interesting,” Cas mused. Dean shrugged. 

“Tell me something about you,” Dean said, eager to change the topic. 

“Like what?”

“Anything.”

“I got expelled from the fancy high school my foster parents were sending me to.”

“No shit?” Dean exclaimed. 

Cas laughed. 

“I’m serious. After a stint in juvie for my brother’s weed I had and shoplifting for him, plus getting in a fight to protect my foster sister, Anna, they booted me. Became an emancipated minor after that family didn’t want me and my brother anymore.”

“How old were you?”

“Sixteen.”

“Wow. Fucking crazy, you are just full of surprises,” Dean said with awe, looking at Cas with his intense eyes. Even in just low streetlights, they were magnificent. 

Cas cleared his throat and looked down. 

“So, you seem smart,” Cas said, now the one to switch up the topic, “how’d you manage to get mixed up with Crowley and them?”

Dean laughed but it was a little bitter and different from his normal, contagious laugh.

“Nah, Sammy’s the brain of the bunch, always has been. Those guys hounded me to join during high school. Sure, I’d buy from them because I knew I wasn’t doing much after high school anyways but I never wanted to get mixed in. I kept saying no until my dad died.”

Cas patiently listened, waiting for Dean to continue and explain. Dean took a deep breath, looked up at the sky and kept talking. Cas watched his face as he talked. 

“Apparently, Crowley gets the businesses on his turf to pay for protection from the other guys, Michael’s crew. If not, you get hurt. My dad and Bobby had been paying them off but the garage was hurting when we lost him. We didn’t have that kind of money.”

Dean looked down at his hands as he scratched at the edge of a thumbnail. 

“So, I joined. Otherwise, they would have hurt Bobby or tried to get Sam to join. I had no choice.”

“I’m sorry, Dean,” Cas said after a pause. 

“Thanks, Cas. Only Benny, Bobby and Crowley know that’s why I joined. I keep Sam in the dark, too.”

“To protect him,” Castiel said, trying to reassure Dean.

Dean scoffed. 

“That’s what I tell myself. I just don’t want him to think I’m a lowlife gang member, you know? Hell, if my parents knew…” Dean shook his head.

Cas reached out and grabbed Dean’s hand without thinking.

“It’s okay, Dean. You’re not a machine.”

“It feels like I’m just going through the motions sometimes. But I feel like I can open up with you.”

“I feel the same. You know about as much about me as my brother and I’ve only known you for a week and a half,” Cas smiled, squeezing Dean’s hand who returned the smile and the squeeze. 

Dean’s eyes darted down and landed on Cas’s lips before returning to his eyes. Cas’s heart beat quickened and his face got warm as Dean leaned in.

Their faces were about an inch away and Dean’s eyes were starting to close when Castiel interrupted him.

“Dean,” he said softly, barely above a whisper. 

He didn’t move his head back at all or let go of Dean’s hand. Dean opened his eyes but didn’t move his head back at all either.

“Give me a reason not to and I won’t,” Dean said just as softly. 

Cas opened his mouth to say something, anything, but his mind was only focused on Dean. His eyes, his freckles, how close he was, his lips…

Cas’s eyes stopped on Dean’s lips. He wondered what it would be like to kiss them so he decided to find out. He closed the gap between them, pressing his lips gently on Dean’s.

Dean tasted a little like cigarettes but Cas didn’t mind. The rush he felt through his entire body, blood pumping and roaring in his ears, made him hot all over. It was overwhelming in the best way. 

He let go of Dean’s hand to put one on his shoulder and the other at the back of his neck. Cas pulled him closer as he ran his fingers through his hair, which was incredibly soft. 

They broke for air. Castiel took a couple of slow breaths then opened his eyes. Dean was grinning next to him. 

“You’re a good kisser,” he said, “but I’ll need a second opinion.”

Dean began kissing Cas again, whose hands hadn’t moved, and gradually moved on top of him. The kiss grew more heated as Dean straddled Cas’s lap. Dean slid a hand under Cas’s black T-shirt, making Cas moan into Dean’s mouth. Dean kissed with more fervor, grabbing Cas’s face and pushing his tongue into Cas’s mouth. 

Everything stopped as a bright light caused them to break apart. Dean got off of Cas and they both put a hand up to shield their eyes.

“What the fuck?” Dean cursed. 

“Evening, gentlemen. Hope I’m not interrupting anything.”

“Henriksen, you dick,” Dean spat.

“Watch it, Winchester,” Henriksen said, all joking aside as he lowered his flashlight out of their faces. 

Cas was pretty sure both of their faces would have been a sight, messy hair and too red lips. He was glad to lose the spotlight.

“You boys mind telling me what you’re doing loitering here, parked where you’re not supposed to be?” Henriksen continued, looking at them both.

“Told you,” Cas whispered.

“Shut up,” Dean snapped. 

“You,” Henriksen said, looking at Cas, “I thought I told you to be more careful after the party?”

Cas stayed quiet and if Dean didn’t know any better, he’d say Cas looked scared. 

“All right, we’re leaving. We get it,” Dean said snidely. 

“Good. I’ve seen enough of you two for a while,” Henriksen said with a smug smile of victory. He stood by his squad car and waited for the boys to get into the Impala. 

As they drove away, Cas still looked a little spooked. 

“You all right, Cas?” Dean asked, looking at him as he drove. 

“Yes, fine… I just, I should go home,” Cas stumbled on his words, seemingly distracted. 

“Home? I mean, whatever you want but you’ve tangled with that asshat before and…”

“Please?” Cas pleaded, “just take me home?”

Dean hadn’t seen Cas like this before so he took him home. Cas said a hasty goodbye and got out of the car at his apartment. As a bewildered Dean drove away, Cas ran up the stairs three at a time. He slammed the front door of his dark and empty apartment shut and leaned against the door.

Castiel jumped as his phone rang and he read the caller ID.

 **Henriksen**.

Cas cringed then answered. 

“Hello?”

“Get down to the station. Now. I’m not asking.”

_Click._


	4. Chapter 4

Castiel’s stomach twisted and turned as he walked the several blocks to the police station to meet with Officer Henriksen. This scared him more than any other time he had been arrested. What if Henriksen and Mills changed their minds about the deal? They could arrest Cas or Gabriel all because he had kissed Dean. How could he be so stupid? 

When he walked in, Henriksen was standing in the lobby talking to an officer behind the front desk. The officer looked at Cas and said something to Henriksen who turned around.

His smile faded as his eyes landed on Cas. 

“Follow me,” Henriksen said shortly. 

Cas swallowed hard and headed down the hallway behind Henriksen and got the feeling like he was going to the principal’s office. 

In the interrogation room that Castiel was getting really sick of, Officer Mills was already sitting at the table. Henriksen joined her on one side and Castiel sat across from them, shifting uneasily in his seat. 

Cas glanced back and forth between the two cops before looking at his hands in his lap. 

“Castiel, what happened tonight?” Jody Mills asked. Henriksen opened his mouth but closed it when Mills put up a hand.

“I, uh…” Cas started. He looked up, took a deep breath and continued. “I was at the race and Dean wanted to talk. I said it was a bad idea so we made a bet. If he won, we’d talk.”

“Did he win?” Henriksen asked with a slight sneer. 

Cas glared at him until Officer Mills encouraged him to continue. 

“Yes, he won,” Cas snapped, “so we went to the playground at the school and we… talked.”

“It wasn’t just talking when I showed up,” Henriksen pointed out. 

“What is your problem?” Cas said in a low growl. 

“You’re kind of screwing the investigation if you’re _screwing_ …”

“Okay, okay,” Mills cut Henriksen off, “Look, we’re just concerned that you’re getting too close because that would complicate things.”

“I bought the weed, told you about drag racing and I can keep our deal,” Castiel argued.

“Maybe. But Winchester? Really?” Henriksen jeered. 

Cas was understanding Dean’s dislike for the man more and more. 

“Consider remaining more unattached, Castiel. It’ll be easier,” Mills said. “And if you can’t, then the deal is off. Okay?”

Cas nodded and left the room. 

He took a longer route home to clear his head. It felt like a relief to be let off the hook, for now, but they had a point. Getting attached in any way would be a bad idea. The only problem was that Cas had really liked kissing Dean and didn’t want to listen to their advice.

 

The next few days, Cas reluctantly followed the advice given to him by Officer Mills. Dean sent a couple texts to check on him but Cas opted not to reply. He wanted to, he did, but decided to add some space between the two of them. Preferably, they would make out on the hood of the Impala again without anything interrupting them but Cas couldn’t think like that. 

Cas worked on Sunday, briefly, and again on Monday. There was one text from Dean and a call on Tuesday. Cas felt worse and worse ignoring Dean and finally texted him on Wednesday afternoon to ask if they could meet up. He had to offer some apology and make sure he could still get in the gang to make Henriksen and Mills happy.

Cas: **You free today?**

Dean: **Yeah, sellin with Benny same spot.**

Cas: **Now?**

Dean: **An hour**

Cas: **Ok.**

 

When Cas arrived at the corner, only Dean was there. He was in the shade under the store’s awning again in a black t-shirt and jeans. 

“Hello, Dean,” Cas greeted.

“Cas,” Dean said testily, focusing on his cigarette. 

“Where’s, uh, Benny?” Cas asked, tentatively.

“Inside,” Dean said, sounding very uninterested in talking to Cas, still not looking at him.

“I get you’re pissed, Dean, I do…”

“Do you?” Dean snapped, suddenly furious and glaring at Cas. 

“Let me ex…”

“Explain? Explain how you’ve been ignoring me? I thought we had a good time, at least I did, and then… complete 360 and you ignore me. Did…” Dean shifted into a more vulnerable look, “did I do something wrong?”

“What? No, Dean, I had a good time too… But…”

At that moment, Benny walked out of the store.

“Cas, hey brother, where’ve you been?” he smiled, shaking Cas’s hand.

“Uh, work, mostly…”

“Speaking of…” Benny said. He looked between them and Cas got the feeling that Dean let him in on what happened. “I really got to get going to work myself. Bye, Dean, good to see you, Cas.”

“You too, “Cas said as Dean nodded goodbye to Benny.

“Let’s go for a drive,” Dean threw out. Cas agreed.

 

The first minute or so was tense and silent. Dean sat straight up as he drove instead of leaning back like on Saturday. Both hands were also on the wheel instead of just his right hand on the top and his left out the window. 

“So… you were saying you had a good time Saturday?” Dean said, trying to make light of the situation.

“I did, honestly, it was…” Cas sighed remembering their kiss.

“It was something else,” Dean laughed, leaning back just slightly and his shoulders relaxing. 

Cas laughed too. It was a good description.

“Then, I thought… I thought I messed up. I’m not good at this stuff usually, so…” Dean stammered. 

“You didn’t mess up. I needed time to just…” Cas struggled to get as close to the truth as possible. “Think, I guess? I know that sounds lame…”

“It doesn’t, I get it. We haven’t known each other long, it was a big step. But we need to communicate better, I suppose,” Dean said, turning to smile warmly at Cas as he drove. 

“Yeah,” Cas agreed. 

Castiel wasn’t lying, he did need time to sort everything out. Their situation was just a little more complicated than he was letting on. Guilt burned hot and heavy in his stomach, eating him up, but he didn’t elaborate or explain anything else.

They drove around until they got hungry and decided to meet up with Benny, who had only been covering a couple hours for someone at the diner, at the Roadhouse. 

Dean and Cas grabbed a table and waited for Benny to arrive. Jo took their order, giving a quick hello to Cas before focusing on Dean. To Cas’s surprise, he had toned down the flirting considerably. There was less smiling, less winking…

“Dean,” Cas began.

“What’s up, Cas?”

“I noticed you didn’t flirt with Jo very much tonight.”

“Well, you kind of got upset last time I did that, so…” 

It was hard to tell in the dimly lit bar, but Cas might have seen a slight pink tint to Dean’s cheeks as he looked down and rubbed the back of his neck.

Cas smiled.

“What are you smiling about?” Dean said, looking up.

“Oh, nothing.”

Benny showed up before Dean could respond.

“What’d I miss?” he asked, sitting down. Dean moved a little to his right to give Benny room, making him closer to Cas’s left around the small table. 

Cas and Dean shared a look then quickly looked away.

“Nothing. We, uh, just ordered,” Dean said, still a little flustered. 

Benny looked between the two of them but then lost interest when Jo returned with their food. He swiped a fry from Dean’s plate before it even touched the table.

“Hey, get your own!” Dean snapped, swatting Benny and pulling his plate in towards him.

“Good idea. Jo, I’ll have the same,” Benny said. She nodded and left.

Cas and Dean both dug in right away. When Benny’s food came, he was distracted enough that Dean decided he could move his leg so that his knee was touching Cas’s. Cas gave him a sideways glance and smiled just a little before looking back at Benny, who was all over his own burger.

“Damn Benny, it’s like you can’t grill your own somewhere,” Dean quipped. 

“Food is better when you don’t have to make it yourself,” Benny responded. 

The rest of the time while they ate included sideways glances between Dean and Cas, accompanied by shy smiles and one bumping the other’s knee while they were about to take a bite and having to try not to laugh. 

Jo came to deliver their check and instead of talking to Dean, she turned to Cas.

“Can I talk to you, Cas?”

“Sure,” Cas said warily and didn’t move.

“Maybe outside?”

“Uh yeah, sure.”

Dean and Benny looked just as confused as Cas felt he did as he followed Jo out of the bar.

“Cas, what’s going on?” Jo demanded as they stopped just outside the door of the bar.

“What do you mean?” Cas played dumb.

“I mean with you and Dean, what’s going on?” Jo asked, crossing her arms over her chest.

“Nothing…”

“Bullshit. I saw you guys at the table, that’s not nothing.”

“Jo…”

“It hasn’t even been a week since you told me you didn’t see him like that and now? What the hell, Cas?”

“I didn’t…” Cas was going to say he didn’t lie to her, he didn’t see Dean like that. But that was then.

“Never mind. I should be used to this by now and you saw him here last time. You know how he is. I hope he at least treats you better than all the bimbos,” Jo shook her head and walked down the alley next to the Roadhouse. 

After she walked away, Cas stood alone feeling pretty shitty. Jo had a point about how Dean usually acted around women but if tonight was any indication, he could turn down his flirting. He hadn’t been lying to Jo about his feelings for Dean, at the time, and it was really shocking how everything was turned around from one kiss.

Cas sighed. His brain basically shut down when he thought about that kiss, he had gotten reprimanded at work for spacing out because of that kiss… How could he not constantly think about it, though? Dean on top of him, his hand hot against his skin under his shirt…

“Cas, hey. You okay?” Dean said, stepping out of the door to the bar. 

The daydream couldn’t compare to seeing Dean in front of his own two eyes. 

“Uh, I…” Cas stammered, focusing on Dean’s lips, which made his brain continue to short circuit. 

Dean was standing right in front of him and was close enough to touch but Cas resisted. 

“Where’d Jo go?” Dean asked, snapping Castiel into focus.

“She got pissed, saw us at the table… Stormed off down the alley. Guess we weren’t too subtle,” Cas explained.

“No,” Dean laughed, “I guess not. Benny made a comment, too.”

Cas wasn’t terribly surprised, Benny wasn’t an idiot and they had been pretty obvious.

“Do you, um… I mean… Do you care?” Dean asked, rubbing the back of his neck, which made Cas smile. “That people see?”

“You rub the back of your neck when you get flustered,” Cas stated.

“I…” Dean stopped, “I do not!” He lowered his hand indignantly. 

“You do.”

“Fine maybe I do, but…” Dean looked at the ground.

“It’s cute,” Cas pointed out.

“It… what?” Dean asked, looking up and meeting Cas’s eyes. 

“You heard me,” Cas said simply. 

He stepped forward and quickly wiped the startled look off of Dean’s face by kissing him, answering the question if he cared that people saw them. After all, they were on a sidewalk in Chicago where plenty of people could walk or drive by.

Cas didn’t give a shit. He had Dean in front of him and he wanted to kiss him again since Dean dropped him off Saturday night, police and better judgment be damned.

Cas put his hands on Dean’s hips and pulled him closer while turning him to make sure his back was to the wall of the Roadhouse and without breaking the kiss, backed Dean against the wall. He wasn’t normally this forward but with Dean he couldn’t resist.

“Fuck, Cas,” Dean mumbled into Cas’s lips before passionately kissing him and easily guided his tongue into Cas’s mouth. 

Cas leaned against him more, pressing his knee between Dean’s legs. It made Dean tighten the grips he had both in Cas’s hair and on his hip. Cas began to move both of his hands up Dean’s shirt. His skin was soft and hot over a pretty nicely toned stomach and chest.

Dean pulled his head away a fraction of an inch to laugh softly and say, “If you’re getting hands-y, maybe we should move this somewhere else.”

“Where do you suggest?” Cas asked in a low, sexy voice that made Dean kiss Cas before answering.

“My car,” Dean said, his mouth against Cas’s neck as he placed hot kisses. Cas leaned his head back and kept his hands under Dean’s shirt. 

“Yes. Your car, Dean. _Now_ ,” Cas said, the last word with enough urgency to get Dean to push Cas back a step, grab his hand and pull him away from the wall towards the Impala. 

Since they had all paid, they figured Benny was fine on his own and didn’t think twice about leaving.

In the driver’s seat, Dean had a hard time starting the car and then driving because Cas was practically in his lap. 

“Cas, holy shit, we’re going to get pulled over…”

The bench style of the seat allowed Cas to be against Dean’s right side completely. He was kissing Dean’s neck and a hand was in Dean’s soft hair and the other was on his thigh.

Both of Dean’s hands were steadfastly at ten and two on the wheel and his knuckles were white.

The car jerked violently to the left and almost into oncoming traffic as Cas moved his hand up Dean’s leg. 

“Fuck…” Dean moaned, “we need to get off the road.”

He pressed the gas pedal down further and they quickly got to the alley the drag racing took place in without Cas distracting Dean enough to crash.

As soon as the car was parked and off, Dean was on top of Cas completely, pressing his back flat against the seat.

“You made me almost crash my baby,” Dean pouted over Cas. Cas had to laugh.

“It’s fine…”

“ _She_ …”

“Does it matter, Dean?”

Dean looked down into Cas’s amazing blue eyes and forgot everything else but the guy they belonged to.

As they made out, they each worked the other one’s shirt off. There was a pause as they both kind of just raked their eyes over inch they could see, taking in the muscles and skin of the other one.

Dean began to undo Cas’s jeans while they kissed again but was interrupted when Cas’s phone rang.

“Fuck, seriously?” Cas groaned.

Cas quickly dug it out of his pants and looked apologetically at Dean before answering.

“What?” Cas snapped. Nothing came to mind that should be breaking this up right now. 

“Hello to you, too, Cassie,” Gabriel answered, sounding bemused. 

“Really not a good time,” Cas said, focusing very hard to keep is voice steady but his voice hitched. Dean hadn’t bothered to stop what he was doing and had moved Cas’s pants down and was rubbing his length over his boxers.

“Yeah well, I wouldn’t be calling if I didn’t have to.”

“What’s wrong?” Cas had to bite a finger to stop from making a sound as Dean kept touching him.

“I, uh… got arrested. Think you can help a brother out?”

“Seriously?” Cas asked, not entirely surprised Gabriel had gotten arrested but extremely annoyed at his timing. 

The shift in Cas’s voice to legitimately concerned got Dean to finally stop moving his hand over Cas in his pants. 

“Unfortunately,” Gabriel said, “can you come get me? What are you doing anyways? You sound kind of out of breath.”

“Nothing,” Cas sighed, smacking Dean lightly on the arm when he laughed. Dean was still very close to Cas and could hear the entire phone conversation.

“Really? Because…” Cas could hear a cop snap that his time was up.

“I’ll get you,” Cas said reluctantly said, “bye.”

Gabriel didn’t even say goodbye as the phone was taken from him. Cas could hear him shout indignantly before the line went dead and hoped he didn’t get himself in more trouble.

Dean was smiling above Cas.

“So, do I get to finally meet your brother?” he joked.

“I think I should deal with this on my own, Dean,” Cas said. Dean made a face.

“Come on, Cas!” Dean said, crawling off of Cas. 

Without Dean on top of him, Cas pulled his pants back up and started searching for his shirt. The conversation with his brother had effectively killed his erection.

“I think it ended up in the backseat,” Dean smirked.

Cas looked and there his shirt was. He leaned over the front seat to grab it, very aware of Dean’s eyes on him, specifically on his ass. 

“Do you have to stare?” Cas said as he sat back down. There was no way he would miss an opportunity to make Dean Winchester blush. 

Dean started to turn a little red and rubbed the back of his neck which made Cas laugh as he put his shirt back on.

“Shut up,” Dean said but with a small smile. “Do you want a ride to the police station?”

“Sure. Thank you, Dean,” Cas answered, “I’m sorry about this.”

“It’s not your fault. I understand the troublemaker older brother… That’s been my job for my whole life,” Dean smiled as he started the car after he put his own shirt on.

“You can meet him… eventually,” Cas said as they drove, “Just not tonight, okay?”

“I get it,” Dean said.

When they pulled up to the police station, Dean asked if he could see Cas tomorrow.

“Sure,” Cas beamed. He couldn’t wait.

 

Cas walked inside the station and was met by Officer Mills. 

“Hi, Castiel,” she greeted.

“Hello. Where’s Gabriel?”

“With Officer Henriksen,” she replied.

Cas tried not to wince too obviously but Mills saw and smiled.

“Oh, he’s not that bad,” she tried.

“I just really don’t think he and my brother will get along,” Cas explained. 

They went back to a different interrogation room than Cas was used to. Cas followed Mills into the room.

“Cassie! Great to see you,” Gabriel said, way too enthusiastically for the situation.

“I’d like to say the same, Gabriel.”

“Oh, don’t be like that…”

“Is he being charged with anything?” Cas demanded of Henriksen.

“No, not officially… but,” he started.

“Then can we go?”

Henriksen gave Mills a look before answering.

“Fine. I wasn’t getting anywhere with him anyways.”

Gabriel got up with a triumphant look on his face and walked out the door with Mills. Cas was going to follow but was stopped by Henriksen’s hand on his shoulder.

“Castiel, wait.”

Cas didn’t answer, instead he focused on putting hate into a glare and roughly snapping his shoulder out of Henriksen’s grip.

“Let me take one guess where you were tonight. Or more specifically, who you were with.”

“Take as many guesses as you like, it’s still none of your damn business.”

“I’d be a little more respectful if I were you,” Henriksen said smugly then leaned in, “I can still try my best to get you and your brother thrown in jail.”

Cas turned and walked out of the room. Henriksen called after him as he retreated down the hallway to leave.

“Get me more information about the gang, Novak, or you’re both screwed!”

 

“Cassie…”

“Don’t start, Gabriel,” Cas answered as they walked home.

“Don’t you want to hear my side?” 

“Your side? You got arrested, there isn’t a side to that.”

“Don’t you want to know why?” 

“Not really,” Cas said. He was being very short with Gabriel, borderline rude, and it probably had to do with the fact that Gabriel had interrupted his time with Dean. 

“You don’t want to talk about me, fine… what were you up to tonight?”

Mental images and sounds crept into his brain at the exact wrong time and he could feel his face get warm.

“Nothing,” Cas replied quietly, watching his feet as he walked. 

“My ass. You were getting some! I know that face. Granted, it’s usually on other people and not you…”

“Gabriel,” Cas said warningly.

“Fine, fine, don’t give me the details. Just know I’m happy for you.”

“Thank you.”

Castiel didn’t mention how it was a bad idea to keep doing what he was doing with Dean and that he should do the “just friends” speech tomorrow. Cas wanted to see him, badly, but seeing Dean made him do crazy things. It made him do things like push him against a wall and kiss him, when he shouldn’t. 

If there was ever a definition of a relationship being called “it’s complicated,” this had to be it. 

They walked in silence until they reached their apartment and both went to bed. 

 

~~~

 

The next day, Cas woke up at about ten and he already had a text message. 

Dean: **When can I see you?**

Cas tried to stop his insides from flipping around, the warmth spreading to his fingertips and the goofy grin spreading across his face but it didn’t help. It all happened anyways.

Cas: **I’m free all day.**

Dean: **Good, let’s meet at the corner then go to the store and meet the other guys.**

Cas: **What time?**

Dean: **Couple hours**

Cas: **Ok.**

Cas sat up on his bed to type and flopped back when he sent the last message. How is he supposed to stop kissing Dean when he’s by him? Or to stop thinking about him all the time or worrying about if he’s okay and just wanting to be with him?

Cas knows one thing with absolute certainty. It hits him and he screams into his pillow in frustration.

He’s fucked. 

 

Cas showed up at the usual corner a couple hours later. Dean was already leaning on the wall and smoking. It was hard not to smile seeing Dean in such a comfortable position, trying to give off his bad boy vibe. Cas had seen the softer side of Dean but this side was still hot.

“Hey,” Dean said, still propped on the wall.

“Hello, Dean,” Cas replied with a smile.

“Benny’s working so it’s just us today,” Dean said as he took a drag of his cigarette. 

Cas wished his heart rate didn’t jump at that fact. It made what he needed to do that much harder. 

“Dean, about yesterday…”

“It was great, we should do it again sometime,” Dean said, his smile all teeth and confidence.

“It was great but…” Cas sighed then looked at the ground.

“But what, Cas?” Cas could practically hear the worry in those three words and the fading smile. 

“It’s just… I don’t think the timing is right for us, you know? And I think maybe we rushed this and it will fade just as fast. I’m not good at relationships or dating, I’ve only really been in one…” Cas rambled and couldn’t seem to stop, “I don’t want us to suffer because we kind of skipped the friendship stage originally.” 

“So…” Dean said slowly, putting his cigarette butt out as he thought, “You’re saying we should just be friends?”

“Yes,” Cas said, glad Dean seemed to get what he said.

Cas felt awful as Dean’s face fell. 

“I don’t mean forever, things can change, but…”

“Kind of… slow things down… a lot?” Dean asked, looking Cas right in the eyes. 

Castiel really didn’t want to cause such hurt in those beautiful eyes. 

“Yes,” Cas agreed, “but things could pick up again.”

“Friends with potential?” Dean asked. 

Cas knew he was trying to diffuse the tension with a joke but his strained smile made it obvious that he wasn’t really laughing. 

“Sure, I like that,” Cas smiled. 

Dean’s smile grew more genuine at that.

 

The two remained on the corner, tense at first, but gradually the awkward small talk became just friendly chat. They talked about work and their brothers mostly, Dean even told Cas about Jess and how he wanted Sam to ask her out already. The kid was old enough, Dean thought.

They stopped selling for the day and got into Dean’s car to head to the store the gang usually hung out at. As they drove, Cas focused most of his energy on not thinking about happened on this seat of this car just last night. The seat against his back, Dean on top of him, hot kisses on his neck…

It was impossible.

Dean seemed lost in thought as well. 

“What are you thinking about, Dean?

“Oh, nothing,” he said, but the hand that grabbed the back of his neck gave him away.

“You’re thinking about last night,” Cas said, a statement not a question.

“What… no, I, uh…” Dean tried hiding but looked at Cas and gave up. “Yeah, I was. How’d you know?”

“The hand on the back of the neck thing you do.”

“Dammit, Cas. You really know me that well already?”

Cas shrugged.

“You’re such a great mind reader, what am I thinking about now?” Dean teased.

Cas figured it was lunchtime about and they had driven past the diner Benny worked at so he made an educated guess.

“Pie?” Cas tried.

“Yeah, but that was easy. I’m usually thinking about pie.”

They both laughed as they pulled into the store’s parking lot. 

As they got out, a few hands were thrown up in greeting but most of the guys didn’t change what they were doing. Most had cigarettes and sat on hoods of cars or leaned against them.

“Hello boys,” Crowley greeted in his signature accent. 

“Crowley,” Dean nodded. 

“Cas, have you met everyone?” Crowley asked. 

“Most, I think, but it’s hard to remember everyone’s names,” Cas admitted. 

Crowley rambled off all of their names as he pointed them out. Cas had met them all but had forgotten which name went to who so this helped. 

There was Jake, one of two black guys, and the one who survived being shot; Gordon was the other. Alastair and Azazel who were both very creepy looking, Dick and his Hispanic buddy Edgar were there too. 

“So, you all sell?” Cas asked, trying to make conversation because their conversations had stopped when Crowley did introductions and they were still staring at him. 

“What are you, a narc?” Edgar asked. 

“A… what?” Cas asked, confused.

“A cop or a rat to the cops,” Dean said to him before addressing them all. “He’s not a narc.”

Cas gulped. This was what he was afraid of and he tried to keep his face neutral. They knew he was fake, that he wanted them all arrested. Well, all except Dean. 

The guys still seemed unsure of Cas.

“He socked Raphael, remember?” Crowley said, “He’s on our side. Take it easy. As I recall, none of you lot brought anyone like Dean here did.”

The conversation was lost on Castiel again. 

“We were looking for people to join when I asked you to come to the party. You keep coming back because you’re awesome,” Dean explained in a quick, hushed tone to Cas. 

Castiel was okay with that. He didn’t really want any of these guys to be his friend. Again, except for Dean. But he would prefer if they didn’t want to kill him. 

Not much went on with these guys here besides an argument between two that almost became a fight before they cooled off. Cas found it hard to relax but knew he needed to so he didn’t blow this. Dean gave him a reassuring smile and that helped a lot.

When they were done hanging out, Dean offered Cas a ride home. 

“Okay,” Cas agreed. 

Dean stopped in front of Cas’s building. 

“We should hang out outside of selling and away from those fucking idiots,” Dean suggested.

Cas raised his eyebrows and opened his mouth but Dean kept going. 

“As friends. Friends do stuff… just hang out. Maybe get food or whatever.”

“I’d like that,” Cas said and Dean visibly relaxed. 

“Okay,” Dean grinned, “I’ll see ya, Cas.

 

~~~

 

In the remaining weeks of June, Dean and Cas hung out as much as possible. They kept it strictly friends even though Cas knew Dean wanted them to be more. It was obvious in how close he would be to Cas as often as he could and the fact that there was usually a text from him waiting when he woke up. They would usually just to be to make plans for the day or a silly fact or a movie quote that Cas wouldn’t understand. Anytime Cas didn’t understand a reference, Dean added the movie to a “Cas Must Watch” list. 

Their plans would either be at the corner or one of their apartments, mostly Dean’s, to watch those movies. Cas had so far seen all of the Star Wars movies and liked them as well as the most recent Batman trilogy. Occasionally, they’d eat where Benny worked and avoided the Roadhouse because of Jo and her temper. Eventually, Cas would work it out with her but he wanted to give her time to cool off. 

Once Sam finally asked Jess out, Cas and Dean took him out for ice cream the night before the date was planned to celebrate. 

“Glad you finally did it, Sammy!” Dean cheered. The three of them were sitting outside on the curb in front of the tiny little ice cream shop, Dean in the middle. Cas and Sam both smiled. 

“Yeah, me too,” Sam agreed with a shy smile.

“What’s the big plan for the date?” Cas asked. 

“Just dinner and a movie,” Sam said proudly.

Dean and Cas smiled at each other but the context of the conversation made it a little awkward and they both looked away.

Cas sighed inwardly as Dean and Sam kept talking. He was afraid being just friends would make things awkward between them. This wasn’t the first time, either. Watching movies, Dean would sit kind of close on their couch or keep flirting or just basically stare at Cas when he thought he wasn’t looking. Cas picked up on all of it but fought not to return those feelings and actions. 

Cas’s master plan was to get information on the gang, everyone but Dean, get them arrested and sent away so Dean would be free and they could be together. He knew it was lofty but he could dream. Then maybe they could go on a date, do the dinner and a movie thing.

“Cas?” Dean asked. Cas turned and Dean was looking at him expectantly. 

“What? Sorry,” Cas apologized. He didn’t mean to space out for so long.

“I said, Sam’s going to go hang out with some friends so I offered to drive you home,” Dean explained. 

“Oh. Oh, yeah. Thanks.”

Cas said bye to Sam and wished him luck on his date tomorrow. Sam’s friends walked up and they all walked away. 

When they got in front of Cas’s apartment, Dean put the car in park and turned to face Cas. 

“Cas, I…” Dean took a deep breath, “I was wondering if maybe you’d… you’d want to go get movie and dinner one night? With me? Or ice cream, just us? I mean, if you want…”

“I would want to, Dean,” Cas assured him. He wanted that more than anything.

“Oh,” Dean smiled, “Oh. That’s great!”

Cas couldn’t help but laugh at his excitement. 

“Can I ask you something, Cas?” Dean wondered, turning kind of serious but his eyes still lit up from eagerness.

“Yes, Dean?” Cas asked softly.

“Can I… can I kiss you?” Dean asked, looking more vulnerable than ever and even a little afraid. 

Cas never meant to make Dean feel scared to kiss him but it just couldn’t work with them, not yet. That didn’t mean they had to stay _completely_ platonic, right? Cas said it could be more. And he wanted more…

Cas nodded and they both leaned in, Cas inching a little closer on the seat to make it easier. 

It was slow and cautious at first and the most gentle out of any of their kisses so far. It stayed soft and sweet and was quick.

Cas was disappointed when it ended and kept his eyes closed as Dean moved his head back a little. 

“I’m sorry, it’s just… I pretty much always want to kiss you and it’s been hard not being able to.”

“You don’t need to apologize, Dean,” Cas smiled. “I enjoyed that a lot.” Even if he was talking about physical need, not necessarily feelings, Cas appreciated Dean was opening up a little with him. 

“So, that can maybe happen a little more?”

“I think so.”

“Okay. Cool,” Dean grinned. 

Cas said good night and headed upstairs. 

 

The end of June and into July was pretty much the same; hanging out, selling and watching movies. There was just more kissing. 

Henriksen would occasionally text asking about information regarding the gang. Cas let him know the names of everyone in the gang, two of which Henriksen didn’t know about and that kept him occupied for a while and off of Castiel’s back. 

Finally, Dean texted and made plans to officially take Cas on a date. Cas had seemed to respond quickly and eagerly and Dean was interpreting it as a good sign. 

The day of the date, Dean woke up a nervous wreck and his stomach was in knots and he couldn’t eat breakfast.

Sam raised his eyebrows as Dean pushed his plate away at their table. It was a Saturday and Dean needed to go to work soon.

“Dean…”

“Sam, I’m already on the verge of puking.”

“Nice. Look, going on dates isn’t that hard. Jess and I had a good time the other night thanks to your advice.”

“My advice?” Dean asked.

“To just be yourself.”

Dean laughed. He had told Sam that and he was glad it worked. But if Cas got to know him more, why would he stick around?

“Didn’t you go on dates with Lisa?” Sam asked.

Dean only had messy dark hair and blue eyes on his brain and honest to God had to think long and hard about the ex Sam was talking about.

“Uh, Lisa? No, we didn’t… really go _out_ much. Kind of stayed in?”

Sam nodded and if he got what Dean was implying, he didn’t let on. 

“Okay, well, can I give you advice?”

“You’re going to anyways so… shoot.”

Sam had to make a bitchface before answering.

“Relax, okay? If he didn’t like you, he wouldn’t have taken care of your drunk ass that one night. Also, you should bring him flowers. That would be nice.”

Dean nodded and felt like he should be taking notes. How did this kid become an expert on this stuff?

“Okay. Relax. Flowers. Okay.” Dean’s eyes were focused on one spot on the table and he was still very tense. 

“You’re not relaxing.”

“Go to school, Sam,” Dean quipped. 

“It’s Saturday, Dean.”

Dean snapped out of it and cracked a smile. 

“Got to keep you on your toes, keep you sharp.”

“I got straight A’s again. I’m pretty sharp.”

“Quit bragging,” Dean said through a wide grin. Of course he got all A’s. One of the many reasons he was so proud of him. 

“Just be yourself and it will be great.”

That line kept running through his head as he got ready and went to work. 

 

Cas shut himself in the one bathroom of his apartment and had been there for quite some time. He couldn’t get his hair to do anything right. 

Apparently, it had been too long. 

“Castiel, what are you doing? Are you getting ready for a hot date?”

“Go away, Gabriel.”

“I have to use the bathroom, come on!”

Cas opened the door to the bathroom. He had a simple light blue button up shirt on with the sleeves rolled up and dark jeans. It was abnormally cool out for a July night in Chicago. 

“Damn,” Gabriel whistled, eyeing him up and down. “You _do_ have a hot date!”

“None of your business,” Cas pushed past Gabriel out of the bathroom.

“Who is she, can I meet her?” Gabriel pried. 

“No you can’t meet him,” Cas said, correcting Gabriel and answering his question. 

“Why can’t I meet him?” Gabriel pouted but accepted the curveball, understanding Cas wasn't particular. 

Cas had to smile. Moments like this he remembered why he cared for his brother so much. 

“CAS AND SOME DUDE SITTING IN A TREE…” Gabriel bellowed as he shut the bathroom door. “K-I-S-S-I-N-G…”

Castiel shut his own door to help block out some of Gabriel’s awful singing. 

Moments like _this_ were when he remembered why he wanted to strangle his brother. 

 

Part of Dean’s day flew by because he got to do what he loved. If he won the lottery tomorrow, he would still show up at Bobby’s shop to work. He’d also bring a huge check to thank the old grouch for everything he’d done for him and Sam. Child services would have been on their case after John died if Bobby didn’t take care of them until Dean was eighteen. He also spotted them to help pay for a cheap lawyer who let Dean get official custody of his brother.

Dean slid in and out from under cars, popped under countless engines and sang the whole time he did it. Bobby let Dean listen to whatever he wanted in the garage as long as it didn’t bother him in the office. Dean went through side after side of _AC/DC_ , _Led Zeppelin_ and _Metallica_ tapes.

“All right, Bobby, I’m out,” Dean grinned, ear to ear, standing in the door of Bobby’s office. 

“What are you so happy about?” Bobby grumbled. 

“If you must know, I have a date tonight!”

“No kidding? Who with?” Bobby said from behind his desk. He sounded like he actually cared, too. The gruff man could be a softy sometimes. 

“You don’t know him but I’ll bring him by the shop someday. See ya Bobby!” Dean practically ran out of the shop to his car. 

Bobby barely got his hand up to flick his hat in a goodbye before Dean was gone.

“Idjit,” he muttered. 

 

Dean had almost the entire contents of his closet dumped on his bed. Nothing looked good enough. 

“Dean, it’s getting late…” Sam stopped in Dean’s doorway, glancing at Dean’s bed.

“Really, Dean?” Sam asked with a silly smile. 

“Shut up and help me pick something,” Dean demanded. 

Sam quickly grabbed a white t-shirt to go under a mostly yellow plaid button up with a pair of pretty faded jeans. 

“Done. Now go. Don’t forget the flowers!” Sam said, his turn to command. 

“How could I forget?” Dean mumbled. The flowers were on their living room table, Dean had picked them up after work and he grabbed them on his way out of the apartment. 

“Bye, Sammy!” Dean called before running down the hall and down the stairs out to his car. 

“Have fun!” Sam called back.

Dean practically skipped to his car and drove like a maniac to get to Cas. He ended up being early and figured he would surprise Cas and show up at his door. 

This way, Dean figured, he can put the flowers away before we go.

Dean mentally patted himself on the back for that one as he snuck in behind someone with a key into the building. He had only been here a couple times since they mostly spent time at Dean and Sam’s place but he remembered the way.

At Cas’s door, he paused, remembered Sam’s advice to relax… and knocked. 

After a minute or so of shuffling around behind the door, Cas opened the door.

“Dean,” he said, surprised.

“Hi,” Dean breathed. He got up here quickly but Cas looked good and that was making the air seem in short supply as well. 

“I, uh… These are for you,” Dean said, handing the flowers to Cas.

“Wow. Thank you, Dean, they’re lovely!” Cas said, taking the flowers and trying to hide his face with them. There was no way he wasn’t blushing right now. 

Once the flowers were settled in a vase, Dean motioned that they should go. 

“Bye!” Castiel shouted back to his brother.

“What? He’s here? Shit! I wanted to… damn it, hold on…” It sounded like Gabriel tripped over something and started swearing more. 

“Let’s go,” Cas said, unable to hold back a grin. 

They could hear a shout of, “He brought FLOWERS?” as they walked down the hallway.

“I do like the flowers a lot, Dean,” Cas said as they waited for the elevator. 

Dean smiled. “Sam might have helped with that one…” he admitted.


	5. Chapter 5

They got to the restaurant for their date and the conversation never dulled. It was a slightly fancy Italian place that neither of them had been to called Giuseppe’s. Dean even pulled out the chair for Cas to sit down in which made Cas blush a little. 

There was talk of Cas’s and Dean’s jobs and when that got old, Dean asked Cas about school. 

“Did you finish high school?”

“Nope,” Cas said, eating the amazing warm bread that kept coming as they waited for their entrees. 

“Me neither. We should get our GED’s!” Dean said, sipping his Coke. 

He hadn’t wanted to try his fake I.D. here and risk getting caught while out with Cas. That would have been more embarrassing than when he got caught with Lisa by her ridiculously strict father. 

Cas seemed to contemplate the idea while finishing his slice of bread. 

“I think we should,” he agreed. Dean smiled. Something about Cas made him want them to do this together. It would be good for them. 

“Then what would you do?” 

“Probably take some English classes at the college that I work at.”

“English?” Dean asked with raised eyebrows. He could have guessed that, considering that Cas worked in the freaking library, literally surrounded by _books_. 

“What, not your forte?” Cas said, a smile hinting at his lips.

“ _School_ wasn’t my forte. I’m surprised I didn’t get _kicked_ out before I dropped out.”

“But you’re smart.”

“A smart-ass, maybe…”

Dean twirled the pasta in front of him that came while they were talking and shrugged. 

“You are smart, Dean. You’ll get your GED very easily,” Cas said honestly. 

Dean knew Cas believed it and he appreciated that even if he didn’t believe that himself. 

“Well, it wasn’t just the smart thing. I would have a hard time getting homework done. I always had to try to work or take care of Sam…”

“What about your dad?” Cas asked nervously. Dean didn’t seem to like to talk about his dad much.

“He wasn’t around a lot,” Dean said, pausing to eat some pasta. “He was a mess since Mom died. He drank and wouldn’t be much help or disappear then come back, saying he tried rehab or some bullshit. Bobby and Ellen helped look out for us and I always took care of Sam, still do. It’s my job.”

“The weight that must have been…” Cas said, not even imaging how Dean, or anyone for that matter, could balance all of that at a young age. 

“It’s fine,” Dean said, clearly wanting to change the subject.

“But…”

“Really,” Dean insisted. 

It wasn’t mean but it was definitive. That conversation was over. Cas nodded and continued to eat his own pasta. 

“What do you want to do with English, Cas?” Dean said, much gentler now. 

“I love writing. Books, poems, everything. I like watching people, you know? Seeing what they’re like, what they do. Then writing what I see or what I pretend their life is.”

Dean couldn’t help but smile. He never saw Cas light up like this and he was glad he found something they could talk about that made him this animated. 

After they exhausted that subject and ate in comfortable silence, Dean continued to smile and moved his foot next to Cas’s under the table, hidden by the long tablecloth. 

“Why are you smiling, Dean?” Cas asked, now smiling, too.

“I’m just happy,” Dean said, leaving it at that. “Why are you?” 

“Because you were smiling. I usually smile when you do, it’s contagious.”

The remainder of the meal consisted of a shared piece of chocolate cake, only because they didn’t have pie, and Dean laughing when Cas managed to somehow get some frosting on his nose. Dean reached across the table with his napkin to wipe it off which made Cas blush like crazy and Dean smirk. 

When the bill came, there was only a slight argument. Dean insisted he pay because he did the asking out and Cas tried to pay for his half but finally Dean ended the argument. 

“You can pay next time, Cas.”

Dean realized the weight of what he said, implying a second date, so he just continued to write on the receipt, now beet red. Cas smiled shyly and drank some of his water.

 

At the movies, it didn’t take long for them to start holding hands. It wasn’t the both-go-for-the-popcorn-at-the-same-time thing either. Cas literally asked if they could and he looked so cute so of course Dean said yes. 

Some of the movie was lost to the two of them because they were both wrapped in thought of what this meant for them. Dates that went well usually led to more dates and then it was a relationship. Neither were ready to start that without careful thought.

Cas looked over and saw worry scrunching up Dean’s face and reached a hand to his cheek to guide him into a kiss. It was quick but did the job. Then, Dean was smiling. 

Castiel insisted he could walk to his door on his own but Dean was stubborn as hell and walked him to his door anyways. That allowed Dean to get what he had wanted all night, a good night kiss from Cas at his door. 

It was hot but sweet and just got _really_ good when Dean left before it got out of hand. Cas had opened his mouth to deepen the kiss and Dean knew it could escalate into something Cas didn’t want, at least not yet, so he respectfully stepped back. 

But it was still perfect and they were both beaming. 

 

Dean came home to Sam waiting up on the couch. 

“Well?” Sam asked. 

Dean, who literally hadn’t stopped smiling since he kissed Cas good night, struggled to form words instead of replaying the kiss in his head. 

“It was… awesome.”

Sam watched a seemingly love struck Dean all the way to his room until he shut his door. 

Those were all the details Sam needed. When he got as few words out of Dean as possible normally, he knew this was different.

 _Cas_ was different and Sam could tell that right away. 

He just hoped his brother was smart enough to see that, too. 

Dean had been trying hard to get Sam and Jess together without even meeting her so Sam promised himself he would make sure his older brother was happy, too. It was the least he could do after everything Dean had done for him.

And Cas seemed to be the way to make Dean happy, a ridiculous and floating on air happy that he just saw proof of. 

Sam laughed to himself, shook his head and went to bed. 

 

It got to mid-July and Officer Henriksen wasn’t happy with how little Castiel had done as an informant. Cas had nearly forgotten about his job because his time and focus was all Dean. It had been a while since he gave any updates to Henriksen or Mills.

Cas only found out his displeasure when Henriksen called him while he was at Dean’s and he ignored the call. Instead, he made out with Dean while they had some movie on the background. 

When Cas finally and reluctantly left Dean’s because Dean had work and called Henriksen back, it had been over two hours and several missed calls. 

“Novak, I swear if you were with…”

“Why did you call?” Cas cut him off with a sigh. Henriksen’s rants about Dean were getting old.

“Can you…” Cas could tell that he was struggling to find the right words, “can you please come down to the station? Officer Mills and I would like to speak with you.”

Cas had to hold back a laugh at how Henriksen was speaking carefully and through his teeth. Cas would bet on pain of never seeing Dean again that Mills was standing right next to him making him be nice. And he wouldn’t make that bet lightly. 

“Sure,” Cas agreed. Henriksen said nothing and just hung up. 

 

At the station, a cup of water was waiting for Castiel as he sat, as usual, across from the two cops. 

“Castiel, thanks for coming,” Mills began.

Cas nodded as he graciously drank the water. The weather was finally realizing it was July and started to act accordingly. It was freaking _hot_ outside. 

“We were wondering if you could get us more information than you have,” Mills asked, sounding a little cautious. 

“Specifically, the locations where the other guys sell,” Henriksen said but practically in a civil tone. 

Cas figured this was why he was nice on the phone and he got water. He was being buttered up but it didn’t matter. Cas couldn’t call them out on it. 

“I could, sure,” Cas said. 

Castiel knew he had no choice. There was no way he was going to jail or letting Gabriel go either if he could help it. If he put the heat on the other guys in the gang, maybe some pressure would be off of Dean.

“Thanks,” Henriksen said, almost in pain by being polite.

Cas left the room before he cracked up and got in trouble. 

 

Cas and Dean sold on their corner with Benny the next day. This was only slightly disappointing to them because they weren’t alone but Benny was nice enough to go into the store and buy a Coke to give them some time. 

They used it wisely. Dean kissed Cas, pressing him against the wall and tasting like cigarettes, and when Benny came back he announced his presence with a small clearing of his throat. 

“Sorry,” Dean said with a shy smile to match Cas’s.

“No you’re not, brother,” Benny laughed. “And you don’t have to be.”

Dean was grateful for Benny and he was growing on Cas, too. 

The three of them relocated to the store’s parking lot after they sold to join everyone else loitering around. 

Benny, Dean and Cas stuck to standing around the Impala and everyone else kind of just gave them space. 

“Does everyone else sell close by?” Cas asked. Dean and Benny both gave him a weird look.

“Just curious,” Cas said defensively. Dean shrugged and they told him. 

Between the two of them, they could tell Cas the streets where they sold in pairs. Alastair and Azazel weren’t far from Dean and Benny’s corner. Gordon and Jake were to the west by a little and Dick and Edgar were further south. Crowley just supervised everything.

“But he still gets a cut?” Cas asked, struggling to remember all three intersections. He wished he could write it down but figured that would make it obvious he was gathering information.

“The biggest,” Dean said bitterly. 

“Hey, you guys coming to Crowley’s?” Jake asked as he walked up to the car, cutting off the conversation. 

“Another party?” Benny asked. 

“You know it,” Jake answered. 

Dean looked at Cas who shrugged. 

“Yeah, probably,” Dean responded. 

Cas had to smile a little because Dean checked with him and seemed like he only wanted to go if Cas went. 

That was fine by him.

 

~~~

 

The Saturday that Crowley had planned another party, Cas woke up to a text from Dean.

Dean: **What are you doing today? I got Bobby to give me the day off.**

Cas: **Nothing. Why, do you have something in mind?**

Dean: **Yes but it’s a surprise. I’ll be at your place soon.**

Cas: **Okay.**

Cas didn’t try to type out his feelings because it was impossible to put them into words. Dean had a day off and he wanted to spend it with _him_. Cas grinned like an idiot and could only guess at what Dean had in mind. 

 

Dean showed up in the Impala as Cas waited on the front stairs of his apartment building. Instead of pulling over on the street to pick Cas up, he went and parked. When he walked back, Cas must have looked confused and Dean laughed. 

“Cas, you gotta trust me a little, man. It’s gonna be fun!” Dean exclaimed. 

“Where are we going?” Cas asked as they started to walk down the street. 

“You’ll see.”

Cas pouted. 

“Oh, all right, I’ll tell you one thing. We’re starting on the train.”

“That’s still very vague, Dean.”

Dean laughed. 

“I told you already, it’s a surprise! Don’t you like surprises?”

“Not particularly.”

“You’ll like this one, I promise.”

Cas looked over at Dean as he walked and saw sincerity in those wonderful eyes that set him at ease. He’d follow him anywhere, explanation or not. 

The two of them rode the Red Line “L” north. Cas couldn’t figure where they were going. After all, it was a big city. “North” in Chicago could mean a lot of things especially if they were starting on the south side. 

It was a mostly quiet ride. Dean seemed kind of nervous and Cas stopped guessing where they were going after a while and switched to talking about anything else. 

They finally got off at Monroe and started walking. A bunch of other people seemed to be headed in the same direction and Cas pieced it together a couple blocks before they got to Grant Park. 

“Are we…”

“Yup!” Dean interrupted with a huge smile, relieved to not keep the secret in any longer. 

“You brought me to the Taste?” Cas asked, a smile pulling at his own lips. 

The two walked under the sign announcing the infamous Taste of Chicago. It was mostly a tourist thing for out-of-towners and suburbanites but Cas was excited anyways.

“I did, I remember you mentioned you’d never been,” Dean said, bashfully rubbing the back of his head.

“This is amazing,” Cas said, looking around at all the food vendors, they ones they could see anyways. 

He thought long and hard and barely recalled saying he wanted to go. It had to have been only once. 

About a month ago.

“You remembered that after a month?” Cas asked, stunned. _There was no way_ , he thought.

“Yeah, I’m awesome like that,” Dean grinned in his signature confident manner. 

Cas grabbed his hand and pulled him closer to kiss his cheek.

“Thank you, Dean,” Cas said softly by his ear to try and make him blush.

He wasn’t disappointed. 

They continued to hold hands as Dean led them to buy tickets to get food. 

Immediately, they headed for Lou Malnati’s to get some deep dish pizza. They sat on the grass under the tree to enjoy it, both of them making several moans as they chewed. 

After they ate, they walked around holding hands to see all of the vendors and occasionally go back under a tree because it was so hot. After an hour of that, Dean suggested they get something for dessert. 

“What would you like, Dean?” Cas asked. 

“How about cheesecake?” Dean asked, stopping in front of Eli’s Cheesecake. 

“But it’s not pie!” Cas faked as if this was a crisis. 

“Hey, I can like other desserts. Pie is just my favorite,” Dean replied as he got them a piece of plain cheesecake with strawberries on top to share. 

They returned to sitting under a tree. Cas, with his third forkful of the creamy dessert, caught Dean off guard and swiped some of the strawberry sauce on Dean’s face next to his lips. 

Dean looked up from the plate that was between them, his mouth in an “O” shape. 

With that look and the sauce on his nose, Cas had to crack up. 

“Oh, that’s funny?” Dean smirked. 

“Very,” Cas barely managed in between laughs.

Dean leaned over the cheesecake to kiss Cas because his laugh was too much. Cas broke the kiss before eating the strawberry sauce off of Dean then kissing him again, making it taste like strawberries. 

“Cas…” Dean said quietly with his eyes closed. 

Cas didn’t say anything and waited for Dean to say something. Dean pressed his forehead against Cas’s.

“I’m glad you came with today. This is awesome.”

“I’m glad, too,” Cas smiled and kissed Dean again. “You plan quite the surprise.”

“So, it’s a good second date?” Dean asked, looking at Cas a little nervously.

“A _great_ second date,” Cas grinned. “Even though I thought I was going to plan the next date.”

“You got the next one, then.”

There was a band playing that Dean liked and Cas didn’t know. Dean insisted that they sat in the grass and listen to for a while and Cas agreed. They seemed to be doing a lot of covers of old rock songs. Cas split his time watching the band on stage and Dean mouthing the words. He looked cute and Cas grabbed his hand.

When the band finished, Cas figured they would just head home. 

“Nope,” Dean countered when Cas guessed that out loud, “the fun isn’t over.”

“Where are we going next?” Cas asked. Honestly, this was already a great day with more than he hoped for and he would never complain about spending more time with Dean. 

“Another surprise, follow me,” Dean said, taking Cas’s hand. 

They left the Taste and started walking. It was a long walk but they finally got to Navy Pier which Cas had only been to once before for a class field trip. It was another thing mostly for tourists but it was nice to get out of their neighborhood. Dean had never been but explained how he looked it all up online which made Cas smile. Dean had actually looked stuff up and put a lot of thought into this surprise date. 

After wandering around the Pier for a long while, it started to get dark and a live band was playing along the walk. They both stopped to sit and listen. Cas could recognize they were covering some songs that he had heard in Dean’s car, just like the band from earlier. 

They sat hand-in-hand on a square concrete bench that was around a huge flowerbox. Cas leaned over to whisper his thanks for a great day in Dean’s ear and then kept leaning his head on Dean’s shoulder as they enjoyed the music. 

Then, the fireworks started. Dean walked with Cas to the end of the pier and they stood over the water watching the fireworks go off. 

Cas watched the fireworks and then Dean. The fireworks lit up his face, changing under the light they provided. There was a childlike joy to his face and Cas deducted that he didn’t get a chance to just enjoy fireworks many times as a kid. Either of them. Well, they could both enjoy them now. 

Cas grabbed Dean’s hand and Dean turned to look at him. Dean looked from Cas’s eyes to his lips then back at his eyes before pulling him in for a kiss. 

When they broke the kiss and watched the fireworks again, Cas knew he was more than fucked now. 

He was falling for Dean Winchester. 

 

Cas and Dean walked back to the train after the show was over. 

They finally got there and were both pretty tired and rode in mostly silence. Cas rested his head on Dean’s shoulder again and couldn’t remember ever being happier. After being bounced foster home to foster home through most of his childhood and having the only constant in his life be Gabriel, this was a nice change. 

But he knew it might be ruined.

Henriksen’s plan was to get Dean, Benny and the rest of them arrested. Cas needed to figure out how to make Henriksen happy enough and keep the people he cared about out of jail. There was a more than likely chance it would go poorly like everything else in Castiel’s life had so far. 

“Cas, you okay? You seem tense,” Dean observed. They were almost back to their stop. 

“Yeah, I’m fine,” Cas said, sitting up to look at Dean, “Just a little tired but today was amazing.”

Dean grinned ear to ear. He was adorable when he got excited, Cas decided. 

“Great! I’m glad you had a good time. I did too.”

They reached their stop and got off the train.

“Do you want to go to Crowley’s?” Dean asked. The party had kind of slipped Cas’s mind. It was pretty hard to remember other people existed when he was with Dean. 

Cas thought about it. He wanted to spend more time with Dean and he didn’t mind if this was how they did it. 

“Sure,” Cas agreed. He shot a quick text to Gabriel to let him know that he was going to stay out so he didn’t worry. 

Dean suggested they drive after so much walking that day so they walked towards Cas’s apartment to get the Impala where they left it. 

As they walked, Cas easily laced his fingers with Dean’s who smiled shyly as he did. 

They walked and talked about what they liked most at the Taste of Chicago when Dean suddenly let go of Cas’s hand. 

“Shit,” Dean muttered.

“Dean, what’s wrong?” 

Dean didn’t have to answer before Cas found out what was wrong. 

“Well, well. Look who it is.” 

Raphael and Uriel crossed the street and headed right towards Dean and Cas. 

They were still out of earshot at the moment and Dean leaned over to Cas.

“When I say run, we go in opposite directions and right to Crowley’s,” Dean said in his ear. Cas nodded.

“What are you boys up to?” Uriel asked as he and Raphael of them blocked their path on the sidewalk. 

“Nothing. Now get out of our way,” Dean demanded. 

“Now that’s not how you want to talk to us, Winchester,” Raphael snapped.

“Why the fuck not?” Dean said, attempting to look bored with the situation. 

“Because,” a voice said behind Dean and Cas, “you’re severely outnumbered.”

Cas and Dean turned to see Michael and Zachariah blocking their path from the other direction.

“Maybe, but we can still take you,” Cas said, attempting bravery when every instinct told him to run. Run fast and run far. He stayed put, holding his ground until Dean gave the word. 

The four rival gang members laughed at Cas’s false bravado. Dean gave him a look that was trying to stay brave as well but his eyes showed his fear. The situation was going south and they had started to close in. 

“Now!” Dean said. He took off up the sidewalk, brushing past Uriel and Raphael. 

Cas sprinted the other way, narrowly avoiding being grabbed by Zachariah. 

_Fuck, fuck, fuck_ , Cas thought with each of his pounding footsteps. 

Zachariah and Michael had followed him, he could hear them, but he didn’t care. He was just hoping and praying to whatever or whoever would listen to keep Dean safe. Cas thought if they got him but Dean was okay then Cas wouldn’t care. 

After a few unexpected turns and detours, Cas seemed to have lost the two on his trail. He started to make his way to Crowley’s, now only walking. 

As he kept walking, he heard a sharp cry of “There he is!” from behind him and began to run again without even looking behind him. 

It might have been stupid but he guessed Crowley’s would actually be safest. There was safety in numbers right? Also, the guys he was running towards hated the guys chasing him so he figured they would help. 

He got to the party and saw Crowley on the lawn.

“Castiel, what…”

“Michael… chasing…” Cas said, slightly out of breath. 

Cas didn’t need to say anything else. Crowley simply whistled and Benny, Dick and Edgar sauntered over from the porch. They stood next to Cas as Michael and Zachariah caught up. They met on the sidewalk in what was essentially a staring contest. 

“Well?” Crowley asked them. It was clear five to two was terrible for the two unwelcome guests and they began to walk away. 

Crowley looked extremely smug and turned to give Cas a nod. Dick and Edgar headed inside and Benny stood next to Cas. 

Zachariah and Michael stopped in the street to talk and were might by Raphael. 

_Where’s Uriel?_ Cas thought. _Where’s Dean?_

The second, of course, was much more important. Cas needed to know that he was okay. 

Benny was talking to Cas but he wasn’t listening. He was listening to the guys in the street.

“Where’s Uriel?” Michael asked in a hushed tone, aware that Benny and Cas weren’t far away.

“He…there was….met up with…” Uriel talked much quieter than Michael and Cas couldn’t hear him very well. Whatever he said seemed to make Michael and Zachariah happy and that made Castiel’s stomach churn. If those goons were happy, it could not be good. 

The three continued to talk and then walked away after throwing oddly satisfied grins at Cas. 

_What could they be smiling about?_ Cas thought. 

“Benny, Dean didn’t come here did he?” Cas asked, beginning to panic. 

“No, I figured he was with you,” Benny answered. 

“He was, we got surrounded by four of them and split up. We were supposed to meet here,” Cas explained. 

Benny shook his head. “I’m sorry brother, he’s not here.”

Cas pulled his phone out and called Dean. 

There was no answer and Cas sat down on the curb. 

_Dean, where the hell are you?_

Cas worried himself about about Dean. He tried calling him again but still no answer. Benny had gone inside to make sure Dean hadn’t come to the party and somehow slipped past him.

As Cas was thinking the worst, he was yanked to his feet and spun around very aggressively. 

“Who the fuck do you think you are?” Alastair snapped. He and Azazel were in Castiel’s face.

“What…” Cas asked, confused.

“You know what we mean, don’t play around,” Azazel said, his gaze creepy as always. 

“I don’t, so explain it to me or get off,” Cas said, annoyed. He really didn’t have time for petty arguments with these idiots when he didn’t know if Dean was okay. 

“We sell on our corner with no problem for a long time and then you show up and we got problems. Henriksen tried busting us today! He’s never been to our corner,” Alastair finally explained. 

“I don’t know anything about that,” Cas lied. 

“Don’t lie,” Azazel yelled as he swung quicker than Cas could blink.

Cas fell to the ground, his cheek throbbing and black dancing at the sides of his vision. He wouldn’t have guessed Azazel could hit that hard. When Alastair punched him in the jaw that was a little less surprising that it would hurt that bad.

He tried to get up but that only got him a swift kick to the side and he fell again. A couple more punches and kicks and Cas was ready to give up. Each hit he was hoping would knock him out. 

“Hey,” a familiar voice yelled, “let’s make it a fair fight.”

Cas found it hard to see because of the swelling of one eye and the borderline unconsciousness he felt. But he had to fight, he had to see…

“Dean,” Cas said, barely audible. He was pretty sure it was Dean but he couldn’t be sure.

“I’m here, are you okay?” Dean said, grabbing Cas’s face with both hands.

“I’m…” Cas coughed, which added to the pain along his ribs, “fine. Are… they gone?”

“Yeah, they don’t want to fight me, I could take them both,” Dean smirked. 

Cas managed a laugh without too much pain. The classic Dean Winchester cockiness never failed. 

Castiel finally managed to get a good look at Dean, despite the lack of light. Dean had a black eye and blood on his face that was hard to tell where it was coming from. His shirt was torn and there was blood on his arm that was slowly drying but made a line down to bruised and bloodied knuckles.

“Dean, you look almost as bad as I probably do,” Cas said, smiling as wide as his hurt mouth would let him. 

“No way, I’m sure I look great,” Dean said, helping Cas up. 

“What the hell happened?” Benny had finally come back. 

“Nothing, nothing…”Dean said, brushing it off.

“When you two have a lover’s spat, you really go at,” Benny joked.

“Hilarious, Benny,” Cas said dryly. 

“Uriel and a couple others got me. We’re going to get out of here,” Dean said, “I’ll catch you later.” 

“Where are we going?” Cas asked, ready to go anywhere Dean wanted. Dean and Cas began to walk down the street. They could both walk on their own but each were clearly in pain and slightly limping. 

“I’m taking you home,” Dean said and winked with his good eye.

 

“Dean…Cas, what… are you okay?” Sam asked as they walked through the apartment’s door. He was at the table with his usual books and everything but jumped up as they clambered in. 

“We’re fine, Sammy. Could you just grab the first aid kit?” Dean asked. “And whiskey.”

Sam sighed and went and got it from the bathroom like it was routine. Dean and Cas sat next to each on the couch, probably closer than was necessary. 

“Why are you still awake?” Dean asked, getting stuff out of the first aid kit. 

“I was worried about you,” Sam said, “and for good reason, apparently.”

“I’m fine,” Dean insisted, “this isn’t the worst that has happened.”

Cas looked at Sam.

“This isn’t the worst that has happened,” Sam confirmed. Cas hated seeing Dean hurt and knew that even worse would be awful to see. He hoped he would never have to see worse.

“We could use some of the frozen peas, too,” Dean said, grabbing some hydrogen peroxide and cotton swabs.

Sam got them and set them on the coffee table next to the whiskey. 

“What can I do?” Sam asked.

“Nothing, it’s fine,” Dean said again, getting impatient. “Seriously, it’s late. We can take care of each other. Right, Cas?” 

Cas was too busy blushing to answer.

“If you’re both going to get all cute, I’m out, goodnight,” Sam said.

“Night, Sam,” Dean and Cas said together. Their eyes didn’t leave each other and they both laughed a little.

“Ew,” Sam said, shutting his bedroom door, making Dean and Cas laugh more.

“Okay,” Dean said, looking where to start first. He silently cleaned Cas’s face up, wincing when Cas did even though it didn’t hurt Dean, until Cas spoke.

“I wish they hadn’t gotten you, I wish they caught up to me,” Cas said.

“Don’t be ridiculous, I’m glad they got me instead,” Dean said, pausing as he cleaned. He handed Cas one of the bag of peas to put on his swollen eye. “But it didn’t really do anything, you still got beat up. What’s their problem?” 

“They said Henriksen crashed their corner today.”

“And?” Dean kept moving the cotton along Cas’s hurt face. 

“And they blamed me,” Cas explained. 

“But you didn’t have anything to do with that! I swear, next time I see them…”

Cas put a hand up and grabbed Dean’s wrist, stopping Dean from what he was doing. 

“Dean, it’s okay,” Cas said softly, looking right at him. 

“No, it’s not…” Dean said, still angry.

Cas, even though it kind of hurt, kissed Dean. It was quick but nice.

“It’s okay,” Cas said again. 

“How is it okay, Cas?” Dean asked. “We’re both beat to hell and I just wanted today to be special.” Dean got a little sheepish with the end and looked down, his voice slightly trailing. 

“It’s okay because you’re okay, Dean,” Cas said, putting a hand under Dean’s chin to lift his head up. “I was so worried when you weren’t at Crowley’s… I thought…”

“That something happened?”

“Yes. Really bad and… I can’t stand that, thinking about losing you? I had to…”

“You had to what?” Dean wondered, grinning with a mischievous glint in his eyes. Cas dropped his hand from Dean’s face. 

“I sat on the curb worried sick, are you happy?” Cas admitted and Dean laughed. How could he laugh?

“I’m sorry, how is this funny?” Cas demanded. “I thought something was terribly wrong… and…stop laughing!”

“It’s not…” Dean said, trying hard to stop laughing but Cas’s face was all scrunched up and now he had crossed his arms. “Not really, you’re just adorable, that’s all.”

Cas’s face softened and he could feel it get warm. The two of them tried to look anywhere else but it was hard when they were so close on the couch. Dean kept his eyes down as he bandaged himself once he was done with Cas. The blood on Dean’s arm had come from a knife slash but it wasn’t too deep. They were both as fixed as they could be.

Dean finally met Cas’s eyes.

“I feel the, uh, same, though, you know? Seeing Alastair and Azazel ganging up on you? I’m…well, kind of shocked I didn’t hurt them.”

Cas knew talking about feelings was not something Dean preferred to do and Cas knew this meant a lot for him to admit all of this.

“I know, Dean,” Cas smiled. The pain in his face and ribs was subsiding. Still hurt, just not as much. He was lucky Dean got there when he did. “And this was still the best day ever.”

“Well, then you must have had some shitty days…” Dean said, almost starting to lean in for a kiss. 

He had meant it as a joke but a dark look passed over Cas’s face who had started leaning too until Dean finished talking and froze in place. Dean quickly remembered all about Cas and growing up in foster care and his trouble with police before and that he most likely _did_ have shittier days. _Much_ shittier days.

“Fuck, Cas…I’m sorry, I didn’t mean…”

“It doesn’t matter, Dean,” Cas said as he stood up. “It’s getting late.” 

Cas started to go towards the door but Dean got up as well and grabbed his wrist. 

“Dean,” Cas said, in a similarly warning tone that he used when talking to Raphael at the race before he punched him. Dean let go.

“Cas, I’m sorry, honestly. Sometimes, I’m an idiot and I don’t think before I speak. Please stay?” 

Dean was practically begging but he didn’t care. He couldn’t let Cas leave angry, especially not in the middle of the night. What if the guys who beat either of them up found him and Dean wasn’t there to protect him?

Cas sighed and checked the clock above the apartment’s TV. It _was_ late. 

“Fine,” Cas said, sounding exhausted. “Your couch was actually pretty comfortable the last time I slept on it.”

Dean turned to get Cas an extra blanket from the closet to hide his disappointment. 

_How did I manage to fuck this up?_

It had been such a great day and if it had gone better and Dean didn’t open his stupid mouth, Cas would be sleeping in his bed. Maybe nothing would have happened, maybe something would have but Cas would have been close to him and not on the fucking couch.

Dean handed Cas the same blanket he used before.

“Goodnight, Dean,” Cas said with finality that Dean took as his cue to leave, not saying anything as he went in his room and shut the door. 

Cas sighed. _Why do I always overact? He was joking, he doesn’t realize what I’ve been through….he hasn’t had it easy, either…_

It didn’t matter, not anymore. Cas fell asleep quickly, a tight frown on his lips.


	6. Chapter 6

Dean found it impossible to sleep. He replayed the entire day in his head, from texting Cas this morning for their surprise second date until Cas icily told him goodnight. There was no doubt it had been a great day.

Mostly. 

Dean groaned and rolled over, pissed that he has been so stupid and careless. 

_What else is new_ , he thought bitterly. _Another thing in your life you messed up._

He continued trying to shut his brain down but all he could think of was self-loathing and how if he hadn’t messed up, Cas could have been in his bed at that moment. The pain from getting beat up didn’t help either. Sleep was clearly not happening so he kept tossing and turning. 

In the dead silence of the apartment, Dean heard a noise, sort of like a whimper. Then something like crying or whining.

“Cas?” Dean asked too softly for anyone but himself to hear. Dean got out of bed and slowly walked to his door, still hearing what he guessed was Cas having a nightmare.

He opened his bedroom door and saw Cas on the couch and he guessed right about the nightmare. Cas was on his back, muttering incoherently and had tears silently streaming down his face.

“Cas!” Dean said, trying to wake him up as he immediately ran over to him. Cas kept freaking out in his sleep.

“CAS!” Dean said, as close to shouting as he wanted to get with Sam sleeping. He shook Cas’s shoulder as well. 

Cas woke up and quickly tried to push Dean away and swung at him without realizing who it was.

“Hey, hey, Cas,” Dean said, grabbing Cas’s fists and sitting on the couch right next to Cas’s side, “it’s okay, you’re okay, I’m here. I’ve got you, Cas.” 

The words were soft and comforting and Cas cried some more and sat up and leaned into Dean’s arms. Dean let Cas cry into his shoulder until he no longer shook and the tears dried up.

Cas sniffed. “I’m so sorry, Dean, I…”

“Cas, don’t. It’s okay.”

Their faces were close and they only needed to whisper. Dean wanted to ask what the nightmares were about but he figured Cas would tell him when he was ready. He was surprised Cas was letting him comfort him after what happened before they went to bed.

“I should apologize for earlier…” Dean started to say when Cas calmed down. 

“I overreacted…” Cas admitted.

“I…oh. Are we…are we?”

“We’re okay, Dean.” Cas said, still seeming pretty shaken up but his small smile held warmth, warmth for Dean. 

Dean grabbed Cas’s face and wiped away some of the tears with his thumbs. Cas leaned into the touch and closed his eyes as Dean kissed his forehead. Dean rested his forehead against Cas’s.

“Dean,” Cas said, very softly and tenderly.

Dean opened his eyes and met Cas’s that were huge, blue and wet at the moment. 

“Can I…um, can I sleep with you tonight?” Cas asked, seeming almost nervous bringing it up.

Dean also figured Cas didn’t mean sex, just actually sleep and that was fine with him.

“Of course,” Dean said. 

He led Cas into his bedroom but was a little awkward. He hadn’t had anyone is his own room for a long time, especially not anyone he cared about this much. Did Cas prefer a side of the bed…or?

“Cas, do you…” Dean turned around to ask.

Dean’s question was cut off when Cas’s mouth was on his. The kiss was all heat and passion and Cas kicked the door shut behind them and pushed Dean towards the bed. He could taste Cas’s salty tears a little on his lips.

“Cas…” Dean breathed. 

He should stop because it wasn’t a good time. It would be taking advantage of him if this continued. Cas looked at him with something that could only be described as hunger, his eyes raking up and down Dean’s body.

It was hot and Dean couldn’t resist.

“I need you, Dean,” Cas said, before kissing Dean again. 

The mattress hit the back of Dean’s knees and he fell backwards with Cas on top of him. 

Dean used every inch of will power he had to put a hand on Cas’s chest and push up enough to get Cas to stop forcefully making out with him. 

“Cas,” Dean said, “now might not be the best… unnh…” Cas had starting sucking on his neck and moving his hips against Dean’s, “the best… time,” Dean continued.

He fought hard to think of words and not about Cas’s hands that were starting to take his shirt off. 

“Now is a great time, Dean,” Cas whispered into Dean’s ear, successfully removing Dean’s shirt then removing his own. “I need a distraction and I rarely feel this strongly about sex.”

“I don’t…” Dean temporarily lost his train of thought as Cas’s lips pressed down on his, “don’t just want to be a distraction,” he finished when Cas paused.

Cas stopped moving his hips and wandering hands, breathing hard. 

“You’re not _just_ a distraction, Dean. I’ve wanted this since the night in your car that my idiot brother interrupted.”

“Me too but… tonight’s a good night?” Dean asked, brow furrowed. 

He did want this, had for a while, but he had to be sure Cas was okay with it. 

“Yes. We had an amazing date today and that’s what I’m choosing to remember. If you want, we can make this day even better.”

“Fuck yeah,” Dean grinned, grabbing the back of Cas’s neck to pull him down for a kiss. 

They both worked their pants off and something dawned on Dean. He’d been with guys before but never all the way. 

“I’ve, uh, never… with a guy, I mean…” Dean stammered, meeting Cas’s eyes but looking a little embarrassed. 

“Neither have I,” Cas said, smiling down at Dean. "I always wanted it to be with someone special."

“So not even with a girl?” Dean asked. 

Cas shook his head, now the one to look embarrassed. 

“Well, let’s make this special, then,” Dean grinned, easing Cas’s worry.

“Can I fuck you?” Cas asked, forward like he only was with Dean.

“Please,” Dean begged.

Cas made quick of their underwear and they were finally naked. The two, still breathing heavily, took each other in and tried to memorize every inch. Cas ran his hand over a few scars he found on Dean’s stomach and chest before leaning down to kiss them. He was careful, like Dean was, of the new cuts and bruises from the day’s fights. 

“You’re beautiful, Dean,” Cas praised. 

“Enough sweet talk,” Dean looked away.

Cas took the chance, while Dean was distracted, to move lower and lick a stripe up the underside of Dean’s very hard dick.

“Oh, fuck,” Dean moaned.

Cas, with pretty much no experience, did a surprisingly quick job of getting Dean to the edge of an orgasm.

“Cas, Cas man, you need to stop,” Dean pleaded. “Wanna come with you in me.”

Cas liked the sound of that and found lube and a condom in Dean’s bedside table. He got busy working Dean open, one finger at a time, loving the moans escaping past his lips. The loudest one came when he crooked his fingers, hitting that sweet spot. Cas put his mouth on Dean’s in a searing kiss to keep him quiet. 

“Ready?” Cas asked, putting the condom on.

Dean nodded.

“Tell me,” Cas commanded. “I want to know how much you want it.”

“Want you, Cas,” Dean pleaded, “Need you in me.”

Cas heard what he wanted and lined his lube-coated dick up with Dean’s hole before sliding in slowly. 

“Fuck,” Cas let out a groan.

Dean didn’t remember hearing Cas saying that word before and his cock leaked precome at the sexiness of it.

“Come on,” Dean encouraged. “Fuck me.”

Cas slid out halfway before pushing back in gently.

“Harder,” Dean begged. “I’m not going to break, let me have it.”

Cas built up a steady rhythm, losing his beat just a little when he felt his climax rising.

“Dean, I’m close,” he moaned.

“Good, me too,” Dean whispered. “Come on, come in me, Cas.”

Cas only needed a few more thrusts before he was doing just that, spilling into the condom as he kept pushing in and out. Dean came too, splashing over his own stomach and getting some on Cas’s. Cas gave a few more thrusts to let them ride it out before pulling out.

“Holy shit,” Dean let out, breathless.

“Yeah,” Cas agreed.

Cas rolled off to throw the condom out before curling up with his head on his Dean’s chest who had grabbed a shirt from the floor to clean them off.

“Good night, Cas,” Dean said, kissing the top of his head. 

“Good night, Dean.”

 

_Pancakes._

That was the first word that came to Dean’s mind as he woke up. A lazy smile pulled at his lips as he could smell the pancakes he guessed Sam was making. He was still under his blanket but realized he was cold as he woke up more. His eyes snapped open as he realized what was missing. 

_Cas._

Where was Cas? He had spent the night, or most of it, in Dean’s arms. Dean still wasn’t wearing any clothes after Cas and he…

Dean smiled at that memory. Then panicked. Is that why Cas left? 

_Fuck. You took advantage of the guy, he never really had been like that with anyone and you messed it all up. His first time, ruined, and now whatever relationship we had…gone. Fucked up because you couldn’t keep it in your pants…_

Dean froze and sat up as he heard laughter. It sounded like Cas and Sam. Dean groaned at the idea of the two of them probably gossiping over breakfast. 

_Whatever_ , Dean thought, _at least he’s still here._

From the floor, Dean grabbed only a pair of sweatpants. The only shirt he found on the floor was one he used to clean himself and Cas up with last night so he threw it towards his hamper. 

Dean sleepily shuffled out of his room. Both Cas and Sam stopped talking and turned to look at him. Cas was sitting at the table with his hair disheveled, probably like Dean’s was, in his own pants but Dean’s old _AC/DC_ shirt.

“Morning, Cas,” Dean grinned and winked, eyeing Cas as he sat down at the table. 

It looked like Cas wasn’t mad at or upset with Dean after all, if his blue eyes going over every inch of Dean’s bare chest were any indication. 

“Hello, Dean,” Cas greeted, looking a little sheepish and looking down. 

Dean loved that Cas could be shy around other people when Dean was flirting but when it was just the two of them, he took what he wanted and Dean would never complain about that. 

Dean turned to Sam.

“What are you smiling about?” Dean asked, accepting the cup of coffee from his brother and began to take a drink.

“Your brother’s happy we had sex last night,” Cas stated blatantly. 

Dean coughed and sputtered on his coffee, his eyes watering. 

“Jesus, Cas…”

“Well, you two weren’t exactly quiet,” Sam grinned. It was a similar smug smile Cas had seen on Dean before. “And it was about time.” 

“All right, all right,” Dean said, grabbing pancakes and hoping to switch the topic to anything else. He knew his face was red and Sam’s face wasn’t helping. “Drop it, Sam.”

They ate and talked about trivial stuff like the weather which was fine by Dean. Sam got up and looked into the fridge, seeing something. Or rather, a lack of something. 

“Uh, Dean… we don’t really have any food.”

“So, go get some,” Dean said, his eyes on Cas as he bumped their knees together. 

If Sam left, he could be alone with Cas and talk. He didn’t particularly want to but he felt like they should. 

“Okay,” Sam answered. “How about some money?”

“In my room, my wallet’s in my pants. On the floor,” Dean said, smirking at Cas.

“Quit bragging,” Sam said, rolling his eyes but smiling. He was glad his brother was happy. 

“Don’t get all healthy shit, Sammy,” Dean demanded, turning in his chair at the table to look at Sam who was almost out the door. "It's too expensive."

“Fine, fine,” Sam agreed, leaving and closing the door behind him.

“He’s probably still going to get mostly fruit and vegetables,” Dean sighed and Cas laughed. 

Dean hesitated before getting to a more serious conversation.

“Cas, I…” Dean started, rubbing the back of his neck before he continued, “I thought you left this morning or something, that I messed up again. Taking advantage of you after what happened. I didn’t, did I?”

“No, Dean,” Cas said, grabbing Dean’s hand on top of the table and interlocking their fingers. “You didn’t mess up at all, I initiated it, remember? I enjoyed last night. A lot.”

Dean smiled, relieved, but was still curious about one thing. 

“The nightmare…” Dean started but Cas shook his head.

“I’ll tell you about it but not yet. Right now, let’s just be happy.”

They each took a bite of pancakes with their free hand.

“I do have a question, though,” Cas wondered. “Where does that leave us?”

The dreaded question. They’d been on two dates and now after they had sex last night, it warranted a discussion.

“Uh…” Dean faltered. His normal smooth-talking abilities didn’t apply to relationship questions.

“I only ask so we’re on the same page, you know? I’m fine with whatever you want,” Cas said gently. 

“Then…boyfriends?” Dean asked. It was very new area for him and the word felt kind of weird to say. 

“I’d like that,” Cas smiled, helping to put Dean at ease. Hell, Cas made everything better just by _being_ there and that kind of scared Dean but in a thrilling, new way.

Dean leaned across the table to kiss Cas.

“But, we…um, shouldn’t tell everyone. Like the gang, I mean. Only Benny should know, I think.”

“Why?” Cas asked, squinting and tilting his head in confusion. 

Dean took a mental picture because it was still adorable every time Cas did that, even if he would never say that out loud. 

“Well, they’re not the most open-minded group of guys, Cas. I don’t want you to get hurt,” Dean explained. 

“You don’t think I’ve been called every name in the book for liking guys, too?” Cas asked, still confused and maybe a little upset.

“No, I mean…I _want_ everyone to know but… I mean, like last night hurt. I don’t want them hurting you. Or anyone hurting you, ever.” 

Dean smiled and gradually Cas did, too. Dean didn’t want Cas to be upset or think he was ashamed at all because he wasn’t. Protecting Cas, even though he knew he was capable on his own, had become a priority in his life. He would protect him like he would Sam because he was family now.

“All right,” Cas said, giving in to Dean’s sweet talk and kissing him over the table again. Their hands were still tightly wound together on the table. 

After Cas and Dean finished eating breakfast and cleaned up, Dean doing the dishes and flicking water at Cas who dried them, they sat on the couch with the TV on. 

Cas looked so cute watching whatever show was on that Dean was going to kiss him when the front door opened and Sam walked in, holding two bags of groceries. 

“You better have gotten real food,” Dean said, getting up to take a bag. Dean looked up from the bag to Sam’s face as Sam shut the door. 

“Sammy, what’s wrong? You look like you saw a ghost, man,” Dean observed, heading to the little kitchen.

“Guess who I ran into at Jewel?” Sam said, almost sounding a little nervous.

“I don’t know, Oprah?” Dean guessed with a smirk, setting the bag down.

“You watch Oprah?” Cas chipped in.

“What? No,” Dean said, defensively but with a silly smile.

“Lisa. Dean, I saw Lisa,” Sam said. That made the smile disappear on Dean’s face.

“And?” Dean asked testily. She seemed like a sore subject to bring up from what Cas had noticed. 

“She’s pregnant.”

Dean nearly collapsed at the news. Sam had to playing a sick joke. His mouth fell open and the bag of groceries slipped from his hands onto the counter with a crash. 

“She…what?” he asked, struggling to find words.

“She’s pregnant, Dean,” Sam said again, joining Dean in the kitchen area. Castiel stayed rooted to the couch, unsure of what to do. This didn’t seem like his business.

“I heard you,” Dean said, snapping out of it. “Fuck.”

He ran a hand through his hair and his eyes stayed glued to the groceries.

“I should… call her? Shit, Sam… how, uh, how pregnant? I mean, like how far along or whatever?” 

“Like four months maybe?” Sam asked. Cas figured they’d have to take the word of a sixteen year old boy until Dean did call.

“Fuck,” Dean cursed as he did the math in his head, “we broke up…”

“Four months ago,” Sam said, confirming Dean’s fear. 

“Shit,” Dean said. 

“Weren’t you careful?” Sam asked.

“Care- of course we were!” Dean snapped. “I’m not an idiot, Sam!” 

“Well, then…”

“I don’t know! Just… let me think.”

Dean had his hands on the counter for balance, eyes wide with panic. Their break-up didn’t end badly, in fact the break-up _sex_ was great. Which was probably exactly how this little problem came to be. 

Cas got up and walked next to him. He had no idea if Dean wanted him to say anything or touch him or how to comfort and reassure him. They had only known each other for two months and suddenly that seemed like no time at all. Last night, Cas had never felt closer to someone else but now… 

“I’m sorry, I should go call her,” Dean said, interrupting Cas’s thoughts. He looked up, at Cas, and opened his mouth to speak but shut it again. 

He headed into his bedroom and shut the door. 

To say that standing there with Sam was uncomfortable was an understatement. Cas said a hasty good bye and left. He would just have to talk to Dean later.

 

Castiel had plenty of time to think about the events of last night and this morning as he walked home. Dean was calling Lisa and couldn’t drive him and besides, they had left the Impala at Cas’s yesterday before their amazing second date. Everything was great until Sam came back with the news of a pregnant ex-girlfriend of Dean’s. Their happy little morning had come crashing down leaving Cas feeling empty and alone.

Cas clenched his fists and realized the thought of Dean having ever been with anyone else, even though he’d seen it before at the Roadhouse, made him angry. And jealous. 

His fists unclenched with a small laugh. He was actually jealous. This didn’t usually happen. His one brief girlfriend, April, had always thought him devoid of emotion but that couldn’t have been farther from the truth. He was just devoid of emotion for _her._

Dean made him feel all kinds of emotion and the past twelve hours alone had been a roller coaster of them. Joy, hurt, anger, shyness, lust and affection…

Last night had been incredible. Even though they started pretty passionate and rough, they had slowed everything down to make sure they were both ready every step of the way. Even if neither of them had said it yet, Cas was pretty sure Dean had showed him how much he truly cared with his body and how he looked at Cas’s own body and touched him.

Cas smiled with ease as he reached his apartment’s building. He knew it didn’t matter what the situation was with Lisa or that they had only know each other for two months. Maybe he didn’t know how to comfort Dean when he needed it but he would learn. 

He loved Dean. 

That was clear now. After last night and wanting to be there for Dean for the whole Lisa thing, he was positive. Sure, he wasn’t about to tell Dean yet that since it was so soon but he could show him that he cared until they were ready to say it out loud.

He pulled out his phone to shoot Dean a text.

Cas: **Call me when you get a chance.**

Cas pressed send as he walked up the stairs. He was still grinning like an idiot as he walked through his front door. Everything would work out, he hoped. Maybe for once, something could go right and he could be truly happy.

“There he is,” Gabriel said with his usual devilish smile from the couch.

“Here I am,” Cas agreed, his smile not faltering as he shut the door. 

“The hell happened to your face?” Gabriel asked.

“The smile…?” Cas asked. Sure, he didn’t smile often but that seemed rude. 

“No, dumbass. Your split lip and black eye. Was it this new boy toy of yours? I will kick his ass into next _month_ …”

“Gabriel, calm down. It’s nothing. And it wasn’t my boyfriend,” Cas started annoyed but couldn’t help smiling again. 

He had never used the phrase “my boyfriend,” since he never had one before, and it felt good to call Dean that. 

No, it felt _great_. So great he had forgotten about the state of his face.

“All right, little brother, but if you need me to beat up some punks, let me know,” Gabriel said, his eyes moving back to the TV but his lips were still pulling up at the corners a little. He was happy his younger brother and the guy who got him flowers were official. Concern was obvious on his face but he knew not to pry. Cas wouldn’t tell him anyways.

 

~~~

 

Dean stood pacing in his room with his phone in his hand. He still had Lisa’s number and was hesitating to pressing “call.” This was going to be a messy conversation. 

_Fuck_ , Dean thought, _everything was going so well…_

Everything with Cas was great and this came along and ruined it. He was pretty sure he heard Cas leave without telling him goodbye. 

“Call her before you walk a hole through the floor, Dean,” Sam called from the living room. That was the problem with living in a tiny apartment, you could hear everything. Sam found that out last night.

“Shut up,” Dean threw back. He was right, though. Dean took a deep breath and called. 

“Hello?” a voice answered after a couple rings. 

“Hi, Lisa? It’s, uh…”

“Dean, hi,” Lisa answered.

“Oh, I…” 

He didn’t know she would have his number still since it had been a while since they talked.

“I figured you’d call. Sam talk to you?”

“He did, said he saw you…”

“And he told you that I’m pregnant,” Lisa said directly.

“Right to the point, okay,” Dean laughed a little, “yeah, that’s why I called.”

“You don’t have to worry, Dean…”

“I’m a little worried,” Dean interrupted.

“It’s fine, you don’t have to worry like you always do. I’ll be okay.”

“But, I mean… it could be… Couldn’t it be mine?” Dean didn’t really know what she got up to after they broke up or how quickly. It could be someone else’s completely but he wanted to know. 

“Maybe,” Lisa sighed, “that doesn’t make it your problem. You didn’t ask for this.”

“Neither did you,” Dean argued. 

In no way would he ditch her if that baby was his. He wasn’t like other guys in their neighborhood. That was shitty and he wouldn’t do that.

“What if it’s not yours?” Lisa argued back. 

“Then I can still be there for you as a friend,” Dean said. Their relationship, while it crashed and burned, had been important to Dean and Lisa was still a good friend. 

“Thank you, Dean,” Lisa said, sounding relieved and like she was smiling.

“Let me know if you need anything,” Dean said. They said good bye and hung up. 

 

Castiel didn’t expect Dean to call him. He figured he was a little preoccupied with everything that was happening with Lisa. Sure, he _wanted_ him to call, but that was different. 

So, when Cas’s phone rang and he saw Dean’s number, he was more than a little surprised.

“Hello?” Cas answered. 

“Hey, Cas,” Dean said. Cas could hear him smiling through the phone and he did, too. 

“Hello, Dean. How are you?” He would have directly asked about Dean’s phone call with Lisa but he figured this would get the conversation there. 

“Uh, good, mostly. I talked to Lisa. She told me not to worry…”

“So, of course, you will,” Cas said.

“Of course,” Dean agreed. 

“What are your plans for the day?” Cas asked, changing the subject. Talking about Lisa reminded Cas that Dean hadn’t always belonged to him and he didn’t like that. 

“Work, soon,” Dean said. Cas grinned as he pictured him checking his watch.

“Your car is over here,” Cas reminded him.

“Shit, I forgot,” Dean sighed. “I have an idea! I’ll walk over and we’ll go together.”

“To the garage?” Cas asked.

“Yeah, then, you can meet Bobby!” Dean said, excited.

“I’d like that,” Cas smiled, “I’ll see you soon.” 

 

Dean picked Cas up a half hour later. Cas had showered but put Dean’s _AC/DC_ shirt back on because it smelled like him and was really soft.

“Nice shirt,” Dean smirked as Cas got into the Impala. 

“Thanks, it’s my boyfriend’s,” Cas smiled and moved closer to Dean to kiss him. 

“I’m starting to like that word a lot,” Dean smiled against Cas’s lips. Cas laughed as Dean started the car and they headed to Bobby’s garage. Castiel was starting to like that word a lot, too. 

When they got to the garage, Dean introduced Cas to Bobby who was in his office wearing his usual plaid shirt and baseball hat. 

“So this is who got you all worked up for that date a few weeks ago?” Bobby asked, looking at Cas with a sort of amused look. Dean looked down at his shoes. “Kid acted like he’d never been on a date before.”

“All right, Bobby…” Dean was red all the way to the tips of his ears and rubbed the back of his neck. Cas put all of his effort in not laughing for Dean’s sake. 

“It’s my job to embarrass you, you know that. Now, those cars aren’t going to fix themselves,” Bobby answered.

“Got it,” Dean said, relieved to leave before Bobby said anything else embarrassing.

“Nice to meet you, Bobby,” Cas said as Dean practically dragged him out of the office. 

“You too, Cas,” Bobby called as they exited.

Dean quickly turned to the radio to get something playing to distract him. He could feel Cas’s eyes on his back.

“Stop that,” Dean said, popping in a AC/DC cassette. 

“Stop what?” Cas asked with mock innocence. 

Dean hit play and turned around. Cas was leaning against the first car he was going to work on with his arms crossed. 

“No staring,” Dean said, walking over to stand right in front of Cas. He didn’t actually mind the way Cas looked at him or how often. 

“Can’t help it, you’re kind of attractive,” Cas said with a small smile, his eyes flicking down to Dean’s lips briefly. 

“You’re not too bad yourself, Cas,” Dean said before kissing Cas. 

He leaned into him, pressing Cas’s back against the side of the car. One of Dean’s hands was on the back of Cas’s neck, teasing at his hair and the other was on his waist. Just as he was sliding his hand under Cas’s shirt, Bobby’s voice called out from his office.

“That’s not what I pay those hands to do. Get to work, boy,” came the good-natured call.

“Yes, sir,” Dean answered. He reluctantly let go of Cas and backed up a step, his face red. 

They spent the next few hours at the garage. Dean worked and talked to Cas as they enjoyed the music and each other’s company. 

When Dean was done for the day, the two of them said bye to Bobby and walked outside. Benny was waiting for them next to Dean’s car. 

“Hey, Benny,” Dean greeted. He didn’t seem shocked to see Benny and Cas guessed he showed up here a lot. 

“Hey, guys. I have some news, can we go to the Roadhouse?” Benny asked.

Dean and Cas looked at each other and shrugged. Benny seemed excited and anxious so it hopefully wasn’t bad news.

The Roadhouse was a good idea, Cas thought. It was about time he smoothed things over with Jo. He only met her twice but didn’t care to have her as an enemy or even just mad at him. If he kept hanging with Dean and the rest of the gang, they would probably be coming here a lot.

The three of them got into the car and headed to the Roadhouse.

“I didn’t know you liked _AC/DC_ , Cas,” Benny observed from the backseat. 

“I… oh, the shirt. It’s actually Dean’s,” Cas grinned.

“Oh… _oh_ ,” Benny said, putting two and two together before he laughed. Cas and Dean glanced at each other before joining. 

 

Once at the Roadhouse, Cas immediately went to the bar to talk to Jo.

“Hello, Jo,” he greeted.

“Cas,” Jo said shortly, focused on the drinks she was pouring. 

“I wanted to apologize again…”

“No need to apologize,” Jo said with a sincere smile at the apology. “I knew he never liked me like that, I was just too stubborn to see it. Just take care of him, okay?” 

Jo was being a lot more understanding than Cas expected and he was grateful. Dean and their relationship had kind of taken Cas by surprise and he hadn’t meant to step on Jo’s toes or hurt her.

“I will,” Cas said. He headed back to Dean and Benny.

“Okay, what’s this news?” Dean demanded. Cas was pretty curious himself. 

“Andrea and I are engaged,” Benny announced with a proud smile. 

“Really?” Dean asked, dumbfounded. Cas was equally shocked. For a couple that seemed to fight a considerable amount, this seemed like a huge step. 

“Yes. And we want the wedding to be pretty small, probably the first weekend in October.”

“That’s…soon,” Cas pointed out. 

“Yeah, well… Guys in our line of work don’t have much in the way of a lifespan. Figured, life’s short, why not?” Benny explained. “Dean, I gotta ask…”

“Yeah?”

“Will you be my best man?”

“Of course!” Dean exclaimed.

“Thanks, brother. And Cas, you’ll be a groomsman, right?” 

“Sure, Benny,” Cas agreed. 

“I’ve actually got news for you to,” Dean said, hands playing with the paper around his beer bottle.

“What’s that?” 

“Remember Lisa?”

“Yeah, what about her?”

“She’s pregnant.”

“Shit!” Benny said rather loudly, turning a couple heads in the bar. “Is it yours?” he continued, in a softer voice.

“No idea, I just told her I’m here for her for whatever.”

“Wow.”

“Sums it up,” Dean agreed. “When did we get so fucking _old_?”

“I don’t know, man,” Benny shrugged. The three of them laughed and ate their burgers when they showed up. 

“They” unfortunately meant Azazel and Alastair who were accompanied by Crowley. Castiel’s stomach dropped but he tried to keep a straight face. Dean gave his hand a squeeze under the table before letting go. 

“We’re figured we’d find you here,” Alastair said, creepy as usual. One look from Crowley and he shut up and looked at the ground. 

“I see my boys did quite a number to your face, Cas,” Crowley said, more smug than he normally seemed. 

“That’s bound to happen, seeing as it was two on one,” Cas said, casually eating a fry. 

Dean glanced at Cas with a smile before turning back to Crowley. He loved when Cas was a badass, plain and simple. He nudged Cas’s knee under the table in silent support. 

“See, they did it because they are under the impression that you are snitching to the cops,” Crowley responded, his two attack dogs still obediently quiet at his side. 

“Cas would never…” Dean started to defend Cas but was interrupted by Crowley. 

“Watch it, Winchester, you’re on thin ice considering you are the one who’s been bringing him around,” he jabbed before turning back to Cas. “If you _are_ a snitch…?”

Crowley trailed off which was scary enough.

“Let’s hope for both of your sakes that you’re not. These two don’t play nice,” he gestured to Alastair and Azazel. 

Before Crowley left the bar, he shifted his eyes one more time between Cas and Dean. He nodded subtly like he knew something or figured something out. His lips curled into something like a smile but it was twisted and wrong. 

Cas was terrified.

Dean gave his hand a squeeze under the table which helped a little.

 

~~~

 

July melted into August and Cas spent more and more nights at Dean’s. They both continued to work and sell on their corner. Benny wasn’t around as much because he had a lot of planning to do for the wedding and according to him, he and Andrea and a lot of different ideas they were working out. There was nothing new with Lisa and her pregnancy and Sam continued to hang out with Jess as much as he could. Crowley, if he was still worried about Cas being a snitch, hadn’t said anything. 

On the first Saturday of the month, Cas decided he was going to treat Dean to a surprise date like he did for him. It was a ridiculously hot day and Cas decided a trip to the beach would be a good idea.

Cas: **Are you home?**

Dean: **Yeah, y?**

Cas: **Let me in, I’m outside.**

Cas patiently waited outside of the apartment building until Dean came outside with a huge smile on his face. 

“To do what do I owe the pleasure?” Dean asked.

Cas kissed him before he answered. 

“I’m taking you on a date,” Cas said, arms still around Dean. 

“Really? Where to?”

“The beach,” Cas said. 

“Aw, you ruined the surprise!” Dean said, pretending to pout. 

“I told you, I don’t like surprises.”

“Yeah, but I do!” 

“Then you shouldn’t have asked.”

Dean laughed. “Fair point. Let me get changed.” 

 

After Dean ran upstairs to change, he drove them both to a beach on Lake Michigan. 

They set up their towels and headed to the water’s edge where they found out that it was freezing. Their feet were in barely an inch of water and it was like ice.

“Nope, too cold,” Dean said and started to back up. Cas grabbed his hand to stop him.

“It is not, don’t be a baby,” Cas said, pulling him back into the water. 

Dean narrowed his eyes. Cas figured that would work to get him to stay in the water. 

“Fine,” Dean said. He began to walk into the water, pulling Cas with him. 

They got knee deep and had to stop because it was too much.

“All right, hold on,” Cas stopped them. 

“Now who’s the baby?” Dean teased. Cas dropped Dean’s hand. “What?” Dean asked. 

“I dare you to go underwater.”

“I dare _you_ to go underwater,” Dean responded. 

“I said it first,” Cas retorted. Dean’s answer was to pull Cas into a kiss instead. 

“You’re cute when you’re demanding,” Dean said. Cas smiled. He was going to answer but before he could, Dean tackled Cas under the water. 

Cas came up sputtering and Dean was laughing. 

“You… you ASS!” Cas cursed. 

Dean was laughing too hard to say anything to that. Castiel couldn’t stay mad at Dean for long and cracked up too. 

“Let’s get out of the water, it’s freezing!” Dean said and Cas agreed. As they walked out of the water, Cas pushed Dean over into the water. 

As Dean stood back up, he was still grinning like crazy. 

“All right, truce!” he called.

They walked hand in hand back to their towels and ate the sandwiches Cas brought with. 

“You know the way to a guy’s heart, Cas,” Dean said, taking a bite. 

“I’ve heard it’s through his stomach, yes,” Cas said, biting his own sandwich. 

“This was a great idea, Cas. You’re the best,” Dean said, still focusing on his sandwich. 

“Thanks,” Cas smiled. 

He swallowed his guilt and tried to focus on their date instead of his deal with the police.

 

~~~

 

The first week of August was more of the same until Henriksen and Mills called Cas into the station. He was with Dean but had to make up an excuse to leave even though that was the last thing he wanted to do. Lying to Dean was terrible but he just had to find a way to figure this all out. He needed more time. 

Cas sat down at the table across from the officers. 

“What’s up, guys?” Castiel asked. 

“We need to know where their product comes from. The big picture,” Henriksen said. 

Cas nodded. 

“How is everything going with those guys?” Mills asked. 

“Um, good, mostly. Well, except when two of them beat me up because they think I’m working for the cops.”

“You are,” Henriksen observed. 

Cas shot him a bitchface Sam would have been proud of.

“Obviously I’d prefer that they didn’t know. How can we fix that?”

“We could arrest you in front of them,” Mills suggested. 

Cas thought it over and nodded. 

“All right, we’ll set something up. Keep us updated to anything, drag racing or parties or whatever they get up to, okay?” Henriksen said. 

Cas nodded and Henriksen left the room. Mills was about to follow him when Cas stood up and stopped her. 

“Officer Mills…”

“Jody,” she insisted with a warm smile. 

“Jody, I have a question. Is there any possibility Dean stays out of this?” Cas asked.

“We only have proof from you that he sold to you once. If he gets out now, there is a possibility.”

“Thank you,” Cas said, grateful. 

Jody smiled knowingly. If there was any chance he could hide how he felt about Dean from her, it was gone now but Cas didn’t care. He had to keep his boyfriend safe as much as he would keep himself or Gabriel safe because Dean would do the same for him.


	7. Chapter 7

The Saturday before Sam would start school again, Dean was working when he got a text from Cas that said he should come over. Dean almost threw down his tools and ran out of the garage then and there but texted back he had to wait until work was over.

Those hours dragged until Dean could finally leave. He tried to focus on the cars and his music but thoughts of Cas kept interrupting. If he wasn’t so good at his job, the distracting thoughts would have caused him to mess something up.

“See ya, Bobby!” Dean said at two, sticking his head in the office briefly with a huge grin.

“Going to see that boyfriend of yours?” Bobby asked, a sly smile barely pulling at his lips. 

“That obvious?” Dean responded, smiling bigger. 

Bobby nodded and Dean laughed before dashing out to his Impala and flooring it to Cas’s. 

At the front door, he got buzzed in and ran up to see the front door to Cas’s apartment was open. Dean walked in semi-cautiously, always prepared for the worst. His hand went immediately to the back of his jeans were his gun always was. 

“Cas?” Dean called, worried. 

“In here,” Cas’s voice rang out from his bedroom. 

“Hey Cas,” Dean greeted, relieved to see Castiel relaxing on his bed. 

“Hello, Dean. I missed you,” Cas said with a smile, not getting off his bed. 

“You saw me yesterday,” Dean retorted. He kicked his boots off, put his gun in one of them, and joined Cas on his bed, giving him a quick kiss. Cas had one earbud in. Dean laid down on his side, facing Cas. 

“So? I still missed you, you smartass.”

Dean laughed. “I missed you, too. What are you listening to?”

Dean put the other earbud in. It was classical music.

“What is this?” Dean asked, biting the inside of his cheek to not laugh. He hated when anyone made fun of what he listened to, mostly Sam, and he didn’t want to be hypocritical. 

“Classical music. I find it relaxing,” Cas said, closing his eyes. 

Dean had to agree, it was nice. He picked up Cas’s iPod and scrolled through the songs. Besides the classical music, there was a lot of stuff he liked, too.

“Cas…”

“Yes, Dean?” Cas opened his eyes.

“You have _AC/DC_ , _Led Zeppelin_ …” Dean kept scrolling, finding many surprises among the Beethoven and Mozart. “ _Journey_? _Metallica_?”

“I got those after being in your car and hanging out with you,” Cas said, looking a little sheepish. 

“So, I’m a good influence,” Dean smirked. Cas rolled his eyes with a smile. 

Dean put on “Faithfully” by _Journey_ and Cas laughed.

“What’s so funny?” Dean demanded, although he didn’t mind. He could listen to Cas laugh anytime. 

“Do you know why I have this song?” Cas asked. 

“It was on the radio first night you were in my car. Sam and I argued about leaving it on,” Dean grinned, recalling that night well.

“Exactly. You’re such a sap but I love that you remember,” Cas said, grabbing one of Dean’s hands. It was dangerously close to “I love you” but still carried a similar sentiment. 

“You remembered, too. Enough to put it on your iPod so we’re both saps,” Dean pointed out. 

“Smart ass,” Cas said again, kissing Dean. 

“Knew I liked this song,” Dean smiled against Cas’s lips, resting their foreheads together. Cas casually ran the thumb of his free hand over Dean’s necklace.

“You always wear this,” Cas observed, eyes on the necklace and inviting Dean to talk if he wanted. 

“Sammy gave it to me when we were little, for Christmas. It was going to be for our dad, I think, but he never showed,” Dean laughed bitterly, one short bark that worried Cas. 

“Did you want to…”

“Nah, it’s all right. The past is the past, you know?” Dean said, a small, sad smile not quite lighting his eyes the way Cas loved. 

They remained quiet, simply holding hands, as the iPod switched to a classical song that Dean liked right away. It had a calm beginning but with a powerful background that would occasionally surge through to the front. He had no idea how exceptional orchestral pieces could be.

As that song ended, Dean brought up something he had been meaning to for a while.

“Cas, when are you going to tell me about…”

“My nightmares?” Cas asked with raised eyebrows. 

Dean nodded, still amazed at how easily Cas could read him when he didn’t finish his sentences. 

“They used to be worse,” Cas started, taking a deep breath before he continued, “Used to be every night. Now, I’m lucky, maybe once a week? Sometimes less. And they’re not terrible, I just wake up, panicked, then fall back asleep. They actually stopped for a while when I met you,” Cas smiled, glad he was finally telling Dean that. He didn’t know why he didn’t earlier because it made Dean smile, ear to ear. 

“Really?” Dean asked, genuinely glad he had a legitimately positive effect on Cas besides adding good music to his library. 

“Yeah, until…” Cas trailed off.

“Until I brought up shitty days,” Dean cringed. “I’m still sorry about that, you know.”

“I know.”

“Do you want to talk about it?” Dean asked. 

He wasn’t one for heart-to-hearts but if Cas needed to talk, he was there because he genuinely cared. He wasn’t just saying it to get in his pants. Mostly because he already did but also because this was different. _Cas_ was different. It was really the only time he had been in someone else’s bed with clothes on. 

“Not much to tell. I mean, shitty foster homes and juvie? You see stuff, stuff happens to you. People hate you, beat you… Those you care about. And I really shouldn’t have mentioned not being straight,” Cas explained. He could feel Dean’s hands clutch tighter around his. 

“Those fuckers…” 

“I’ve left it all behind, Dean. And I’m stronger because of it,” Cas said, a hand caressing his cheek. “Although this protective side of you is hot.”

Dean laughed and Cas could feel the tension leave his body.

“ _Every_ side of you is hot, Cas,” Dean said, a glint in his eyes as they moved over Cas’s body. 

“Always have to one up me, huh?” Cas asked, pressing their lips together. 

“Why, yes I do,” Dean said, returning the kiss and rolling on top of Cas. So much for staying clothed.

Castiel could let Dean one up him. This time. Especially if they were getting naked.

 

When Castiel and Dean had finished having sex and cleaned up, they continued to lie together in Cas’s bed without clothes or the music from before.

Dean untangled himself from Cas to grab his phone from his jeans on the floor. 

“Fuck, it’s already five,” Dean cursed. Cas furrowed his eyebrows. 

“Do you have to go somewhere?” Cas asked, doing his best to use a low, sexy voice to keep Dean from leaving.

“No,” Dean said, distracted by Cas’s voice, “Yes. Damn. I’m supposed to be selling with Benny.”

“Tell him to sell without you,” Cas said. Anything to get him to stop selling and hopefully stay off of Mills’ and Henriksen’s radars.

“I… Actually, one time wouldn’t hurt. Benny’s a big boy,” Dean grinned, tapping out a text to Benny and throwing his phone on the floor. 

“So, you’ll stay?” Cas pleaded. 

“I’ll stay,” Dean said. 

He climbed back next to Cas, kissing him before pulling him against his chest. 

 

Benny stood on the usual corner, laughing softly as he checked his phone. 

Dean: **Sell w/out me, with Cas. ;)**

Benny didn’t bother with a response because he figured Dean was otherwise engaged. He sold and smoked a few cigarettes for about an hour before Crowley showed up with Alastair. 

“Benny,” Crowley said. Benny nodded in greeting.

“To what do I owe the pleasure, Crowley?” Benny asked, stepping out his cigarette. 

“Where’s Dean?” Crowley asked, always one to get right down to business. 

“In the store,” Benny said, “Needed snacks.”

Crowley ignored the joke and looked at Alastair, jerking his head towards the store. Alastair gave Benny a smug sneer before walking into the store. Benny calmly lit another cigarette as he waited for his story to fall apart. 

Alastair came back out and shook his head.

“Benny, come on. Don’t lie to me,” Crowley drawled. As little as Crowley scared Benny, two on one odds in a fight were never good. “Where is he?”

“Sick. But he didn’t want me to tell you. Couldn’t appear weak,” Benny lied, puffing on his smoke. 

“He’s with Castiel, isn’t he?” Crowley asked. Benny said nothing. Crowley nodded, seeming to take the silence as a yes. 

“Let Dean know we stopped by, will you?” 

With one last smug grin from the pair, they left Benny alone. 

 

When Dean finally decided he should head home because he promised Sam a movie night, it was dark. There were a couple texts from Benny that Dean figured he could read later. Cas was saying a very heated goodbye with his lips. 

“Can I see you tomorrow?” Dean asked. 

“When I’m not working, sure,” Cas answered, kissing him again. 

Reluctantly, Dean left. When he got home, he quickly apologized for staying a little later at Cas’s than he meant to. Sam understood and gave him silly grin.

“Shut up and pick a movie,” Dean said, heading to the kitchen to make popcorn. When it was made and the movie, _The Breakfast Club_ , was on, Dean finally checked Benny’s two messages. 

Benny: **That’s fine, brother. Have fun**

Benny: **Crowley was here, figured u were w/ Cas. not good**

Dean’s stomach dropped. This wasn’t good in any way, shape or form. 

“What’s wrong?” Sam asked, sensing the tension.

“Nothing I can’t handle, just a little trouble with Crowley,” Dean said, more honest than usual. He put his phone on the coffee table and kicked his feet up as well. 

“Who’s Crowley?” Sam asked, confused.

“No one. Watch the movie, it’s your pick.”

“Whatever. Your shirt’s inside out by the way,” Sam smirked, reveling in this small victory.

“Son of a bitch,” Dean said, standing up to fix it. Sam was cracking up as Dean sat back down, warranting Dean to throw popcorn at him before he picked up his phone. 

Dean: **You didn’t tell me my shirt was inside out!**

Cas: **It was too cute.**

Dean: **That falls under ‘boyfriend duties’ just FYI**

Cas: **Duly noted, boyfriend.**

Dean: **;)**

“Texting Cas?” Sam asked, looking bemused. 

“Yeah. How…?”

Sam just raised his eyebrows and Dean shrugged. 

“Shut up,” Dean said with a smile. 

Texting Cas was always enough to put him in a great mood. Especially if he called him cute. And boyfriend. Dean smiled down at his phone, missing Cas even though he saw him a few hours ago.

“So, how’s Jess?” Dean asked, changing the subject. 

“Great! Really great. I’m excited for school to start,” Sam said. Dean rolled his eyes good-naturedly and it was Sam’s turn to throw popcorn at him. “I am! We have some classes together and lunch. And I can see her a lot and we can let everyone know we’re dating.”

“Who knew you were such a romantic, Sammy,” Dean teased. 

“Says the guy who brought flowers for the first date,” Sam teased back, drinking his Coke. 

Dean turned red and drank his beer, not responding. It was true, after all. 

“Would you say,” Dean paused, serious now, “would you say you love her?”

Sam slightly sputtered on his Coke, coughing a little. 

“Maybe? I don’t know. I know I like her a lot and always want to be with her. When something happens, even something little, I want her to be there to share it with me.”

“I think you might love her,” Dean said, slightly shocked at how mature his sixteen year old brother was.

“Are you basing this off of how you feel about Cas?” Sam asked. 

“I… I guess. I mean, I feel what you described but… I’ve never said it. To anyone.”

“Not even to Lisa?”

Dean shook his head. It had really been more physical of a relationship than anything else. 

“Wow. So, you think you love him. But you’re too scared to tell him?” Sam summed up. 

“Yeah,” Dean admitted, embarrassed at how much of a chickenshit he was being. 

It wasn’t like him to be scared. Ever. But Cas came into his life and changed everything. Before Cas, Dean didn’t stay to cuddle or really do relationships besides his one with Lisa. Cas met his family, knew him probably as well as Sam, if not better sometimes. And sleeping with him was special, it was intimate and meant something. 

It was love, wasn’t it? Dean didn’t have much to compare it to. 

How was Dean going to admit to Cas he loved him when he could barely admit it to himself?

 

~~~

 

Crowley had it on good authority that Benny sold without Dean again the following Saturday, that authority being the only one he trusted. Himself. 

There had to be a delicate way to go about this, Crowley figured. Castiel had proven useful but the accusations of him being a narc had to be checked out immediately. Crowley didn’t want to get rid of Cas if he could use him but only if he wasn’t a threat. Threats had to be eliminated. 

But he also needed Dean.

Dean was his right hand man, normally. A great seller, fighter, racer… He was important to this gang and Crowley would be damned to let him go that easily and lose him to a boyfriend of all things. In Crowley’s mind, love of any kind was stupid and a waste of time; guys, girls, didn’t matter. It never made sense to him. Business, he could handle. Deals, he understood. 

Besides Cas, there was something, or someone, that could get Dean to do what Crowley wanted. The same way Crowley got Dean in the first place. 

 

On a hot Saturday night, there was another party at Crowley’s. Benny had arrived with Andrea and Dean and Cas were nowhere to be seen. Crowley didn’t bother talking to Benny because if Dean wasn’t with Benny there was only person he could be with.

On the couch, Meg and Ruby sat next to Crowley on either side. 

“Ruby, the high school is back in session, correct?” Crowley asked. He was sipping scotch, his usual. He didn’t understand the love people there had for fruity mixed drinks with cheap vodka. 

“Yeah, why? Are we recruiting? I think I heard Michael’s been trying to.”

“And you failed to mention that?” Crowley glared. Meg snickered, earning a glare as well. If Michael was stooping low enough to search for members in the high school, he would have to as well, at some point. 

_We could pretend to have standards but desperate times, blah blah blah_ , Crowley thought. 

“They’ve been back for half a week!” Ruby argued defensively. 

“Never mind,” Crowley waved her off. He could deal with Michael later. “I do need you to recruit, actually. There’s one specific person from that high school I want. And you’re going to get him.”

“Who?” Ruby asked, always up for a challenge. 

“Sam Winchester.”

 

~~~

 

Besides Sam having started school, Castiel and Dean followed through on their idea to get their GED’s. Their classes were a few nights a week and it was a pretty big change for them because neither of them had been to school in a few years.

Dean would have stopped going completely if it wasn’t for Cas’s support and encouragement. This wasn’t easy for Dean the first time and it wasn’t easier now. But Cas made sure all of the homework got done and that they studied for every test. 

The teacher, Pamela Barnes, was tough but fair. She always knew when Dean and Cas were talking, goofing around or otherwise not paying attention in the back of the room and would call them out on it every time. 

“This doesn’t make sense. I hate math,” Dean said, dramatically dropping his pencil and flopping his head on the table in his apartment. He forgot how shitty he was at algebra. Or math of any kind.

“Come on. You can do this, Dean, you know you can,” Cas said. 

He picked up Dean’s pencil and handed it him. This had all come back fairly quickly to Cas who maybe just had been trying harder. 

“You know you’re smart, right?” Cas said, trying to reassure Dean. 

“This was a bad idea,” Dean grumbled as he retried the problem in front of him, ignoring Cas’s compliment. 

“It was _your_ idea, babe,” Cas said, turning red immediately after he said it. 

Dean simply raised his eyebrows at him, a smile pulling at his lips. 

“Now, how am I supposed to study with you saying such things and being all cute?” Dean grinned fully as he enjoyed Cas stay flustered. Getting Cas worked up and squirming was something Dean would much rather be doing.

“Whatever, just keep working,” Cas mumbled, looking down. Dean grabbed his hand across his table and waited until Cas met his eyes. 

“All right,” Dean winked, “ _babe._ ” 

Cas laughed. “Asshole.” 

 

Sam walked out of school at the end of the day the following Wednesday with Jess. They were holding hands and he walked her out to where her mom was parked to pick her up. Sam gave Jess a hug goodbye and waved at Ms. Moore. 

As he went back to a bench next to the school’s front doors to wait for Dean to pick him up, a dark haired girl he had never seen before walked up to him. She was smoking a cigarette. 

“You smoke?” she asked, sitting next to Sam on the bench.

“No,” Sam said, wrinkling his nose. He hated when Dean smelled like it and never wanted to try. She shrugged.

“Name’s Ruby,” she said. 

“Sam,” Sam answered. Ruby nodded. “I’ve never seen you around, Ruby.”

“I don’t go here. I did a couple years ago.”

“You graduate?”

“No,” Ruby said, not giving any other explanation. Sam raised his eyebrows.

“So, what are you doing here?”

“I was walking by and you seemed… interesting. Wanted to say hi.”

Sam laughed as Dean drove up. He wasn’t really used to a stranger striking up a conversation with him so casually.

Sam walked towards the car after saying a brief goodbye and Ruby stayed on the bench.

Dean parked and was walking towards Sam.

“Dean, what…”

“Sam, get in the car.”

“Dean…” Sam said, confused. 

“Car,” Dean growled and Sam listened. From the car, Sam watched Dean walk over to Ruby and was dying to know what they were saying. 

“What the fuck are you doing?” Dean demanded as Ruby stomped out her cigarette. 

“I’m sitting,” Ruby said.

“Look, I don’t know what you and Crowley are trying here but it stops. Now. You leave Sam out of this, all of this, got it? I joined so he would never have to. He’s off limits and Crowley knows that.”

“Tell him yourself,” Ruby paused, “Oh that’s right… you’re never around anymore.”

“Just fuck off, okay?” Dean snapped and headed to the Impala.

“How do you know her?” Sam asked when Dean got in, curious as hell. 

“I don’t,” Dean deflected.

“Come on…”

“Drop it,” Dean said, pulling out onto the street. “And stay away from her, you hear me?”

Sam didn’t answer. 

 

Of course, Dean telling Sam to _not_ talk to Ruby only made him want to talk her more. He regularly looked for her after school and he wasn’t sure why. Jess was still very much a part of his life and he would walk her to her mom’s car then look around for Ruby. He couldn’t explain it but she was oddly magnetic. 

One September day after school, Sam had to walk home because Dean was working at the garage. Sam saw Ruby standing on the sidewalk and forgot about Jess. Ruby was technically off of school property because she was warned by the principal to stay away since he didn’t have fond memories of her attendance there. 

“Hi, Ruby,” Sam greeted. 

“Hey, Sam,” Ruby smiled and walked with Sam towards his house.

“So, if you went here, what do you do now? School?” Sam asked. He felt his phone buzz in his pocket but he ignored it. 

“Nope,” Ruby said, hip bumping Sam as they walked.

“Work?” Sam guessed.

“Sort of,” Ruby said, pleased to see Sam getting a little frustrated. 

“Fine, don’t tell me anything. I won’t tell you anything, either,” Sam teased. 

“Well, we’re walking to where you live, I assume, and I know what your girlfriend looks like even if I don’t know her name. And I know your brother.”

“How do you know my brother?” Sam asked, still extremely curious about that. 

“Oh, Dean and I go way back. But that’s his story to tell.”

They continued to talk until they reached Sam’s building.

“See ya around, Ruby,” Sam said.

“Sure,” Ruby said. Sam turned to head into the building. “Oh, and one more thing, Sam,” she called. Sam turned back around.

“What?” Sam asked as Ruby handed him a piece of paper.

“Here’s my number,” she said and with a wink, she left. 

Upstairs, Sam checked his phone. 

Jess: **You didn’t wait after school, everything ok?**

Sam, who had waited long enough to answer her, replied after an inward cringe at his stupid choice to ignore her.

Sam: **Sorry, I’m fine. Just had a lot on my mind I guess. I’ll see you tmo.**

Jess: **All right.**

Sam knew the period at the end of a two word response was never good. Tomorrow, he would have to face an angry Jessica and hope they could smooth this over and avoid their first fight. 

 

~~~

 

“Dean, what’s going on?” Cas asked. They were in Dean’s bed and Dean seemed jittery instead of tired like he usually was after they had sex. They had taken advantage of having an empty apartment and Cas was feeling good but now he was concerned. 

“Nothing,” Dean lied. 

Dean had already explained the trouble brewing with Crowley and his supposed lack of devotion to the gang. Cas knew his boyfriend was still worried. 

“Right,” Cas rolled his eyes. “Just tell me.”

“Fine,” Dean sighed, “I’m a little freaked because Crowley, who’s pissed at me, and Benny are coming to get me soon and I have to go help get a new shipment.”

“Of weed,” Cas clarified. 

“No, copies of _Harry Potter_ ,” Dean said with an own eye roll.

“You don’t have to be a dick,” Cas responded. 

“Come on, you love it,” Dean said, snuggling against Cas’s side. 

“You being a dick? Not really,” Cas said honestly. 

“When am I a dick?” Dean asked, propping himself on one elbow to look at Castiel.

“Right when I met you? The Roadhouse when you got shitfaced?” 

“All right, I get it,” Dean grinned, leaning over to kiss Cas. “But I’m a lovable dick, right?”

Cas’s stomach flipped at the “L” word, still close but not actually saying it, either of them. He wondered how long they could dance around it. Cas nodded with a smile and kissed Dean back as a response.

They both got dressed and walked out to the front of the apartment building. Cas was going to wait until Benny and Crowley showed up to pick Dean up then head home. 

When the car pulled up on the side of the street, Crowley driving, both Dean and Cas stood. 

“Castiel, good, I figured you’d be here,” Crowley said with only a slight sneer. “Get in. Both of you.”

“What? No, you…” Dean attempted, trying to keep Castiel out of whatever Crowley had planned. Dean knew he was pissed at him and didn’t know how far he was willing to go. The entire gang except Benny would be on Crowley’s side if this went south. 

“Shut up and get in. I won’t ask again,” Crowley threatened. They both got in. 

Cas and Dean nervously sat side by side. As much as Cas wanted to reach out and grab Dean’s hand, he figured it wasn’t the right time or place so he kept them folded in his lap. Dean was doing the same thing and Cas could only guess it was for the same reason. 

Right then was a perfect time to text Mills and let her know what was going on. It was a great opportunity to prove he wasn’t a narc or at least pretend he wasn’t and extend the charade if he got arrested with all of them. Crowley, however, continuously checked the rearview mirror to look at Dean and Cas so he couldn’t. 

Cas, despite the severity of the situation, bit his tongue to hold in a laugh. They had arrived at an abandoned warehouse that screamed cliché. He looked at Dean, who smiled, and knew he was thinking the same thing. It made him feel much better. 

Castiel wasn’t sure what Crowley’s plan was but he was guessing they were going to find out. 

Once inside the warehouse, Castiel found that the rest of the gang had assembled already. 

“Dean, almost forgot who you were,” Dick said with a wicked, partial smile. That got a few laughs from the gang. 

“I can still take any of you assholes in a fight so shut the fuck up,” Dean said forcefully. 

“What about Cas here? Think you can take any one of us in a fight?” Edgar jeered. 

“No,” Cas said, then smirked, “I _know_ I can.”

Edgar surged forward angrily to test that but was held back by Dick and Alastair. Cas had taken a step forward too and Dean had protectively stepped in front of him. 

“Everyone cool down,” Crowley’s voice cut sharply across the warehouse. Edgar stood up straight, not planning on charging anytime soon, but kept glaring at Cas. 

“Product should be here soon,” Crowley informed them.


	8. Chapter 8

Crowley gathered the group in a circle as they waited for the product to arrive despite the tension splitting them all in half. Dean, who had stepped back next to Cas, and Benny were one side, backs to the mostly broken front doors, and Alastair, Azazel, Jake, Gordon, Dick and Edgar were facing them with similar scowls. Crowley stood, seemingly neutral, in between them with each group to one side of him. 

It was a tall building with really high ceilings. The only windows were way high up. They were standing in what resembled a clearing in a forest between old boxes and crates of stuff from when the warehouse was used. It was almost a maze, one Cas was all too eager to escape. 

Cas knew that Crowley wouldn’t hesitate to back the other side over their little group of three and the false neutral wouldn’t last if a fight broke out. Crowley’s loyalty was to those he had known the longest and were completely loyal in return. Plus, Cas assumed they all had guns which he did not. 

“Well, isn’t this a cute little group,” came a voice from behind Dean, Cas and Benny who turned around. 

They weren’t keen on having their backs turned to the guys who would as easily stab them as they would breathe but there wasn’t a choice. The big, bad supplier was here and the focus was on him.

“Lucifer,” Crowley said, extending a hand to the newest addition into the shady warehouse. 

Cas detected a little bit of wary hesitation, almost like Crowley was scared of the cool, almost bored looking blonde man. Dean and Benny tensed as the guys shook hands and Cas guessed the rest of the gang behind them did, too. This man exuded a power and confidence that instilled fear. All he had to do was walk in and it was obvious he meant business. The name helped, too. 

Lucifer’s eyes scanned the group and stopped on Castiel.

“Oh, you must be new,” he observed. 

“ _You_ must have been top of your class, very smart,” Cas retorted, sounding braver than he felt.

Lucifer eyed him with new amusement which Cas figured was a bad thing. Castiel could tell Dean was trying hard not to laugh, Cas’s witty rejoinders cracked him up.

“Aren’t you peculiar? People don’t normally talk to me like that,” Lucifer said, even and calm but with an undertone of authority. 

He sauntered a few steps until he was standing directly in front of Cas whose heart sped up. Cas could feel Dean on his right ready to jump in front of him and fight this guy which was comforting but unnecessary. Castiel could handle himself and Dean knew that.

Cas just shrugged in response to Lucifer’s comment while trying to maintain eye contact. The guy had a fierce gaze that made Cas want to look down. Cas could feel Crowley’s eyes glaring a hole through his skull from his left side. Disrespect wasn’t taken lightly by guys like Lucifer, especially in this line of work or this neighborhood.

“Funny, I would have pegged you for the other gang," Lucifer said, still looking at Cas with interest and curiosity, almost like he was trying to solve a puzzle. 

“What are you talking about?” Dean demanded to know as Cas tilted his head to the side and squinted in confusion.

“Winchester, right?” Lucifer commented, sliding his eyes over to meet Dean’s, “Heard a lot about you from Crowley.”

“Yeah, like what?” Dean snapped.

“For one, your lack of respect,” Lucifer said, narrowing his eyes. 

Dean set his mouth in a hard line. His teachers in school always told him he’d end up saying the wrong thing to the wrong person one day and it would get him in a heap of trouble. This might have finally been what they were talking about.

“And how you make stupid decisions to protect those you love,” Lucifer said, his eyes flicking to Cas briefly before returning to Dean with a small knowing smile that terrified Castiel. 

Dean and Cas were both at a loss for words. Crowley must have mentioned Dean joining the gang to protect his brother but he hoped he didn’t mention his theory about Dean and Cas dating. That was ammo in a very dangerous gun.

“Are we going to do this or what?” Crowley said, growing impatient.

“Not yet, we’re waiting for something,” Lucifer said. One look had Crowley standing up straighter and remembering his place.

“Waiting for what?” Crowley asked, curbing his attitude. For the one usually in power, he was clearly not sure how to handle being the subordinate. 

“What the hell is this?” asked the guy who just walked into the warehouse.

It was Michael. 

“For that,” Lucifer said with a malicious smile before making a beeline into the maze of boxes. 

Before Cas could blink, Dean pulled him down to the ground. They crawled on the dusty concrete floor behind stacks of cardboard boxes, old plastic crates and whatever else was piled up to avoid the gunfire. Dean pulled his own gun from the back of his jeans and began to return fire in the direction of Michael’s gang. It started so fast, Cas really only saw Michael and didn’t know how many guys he had brought with him. Castiel had never been more petrified in his entire life.

Someone was laughing, presumably Lucifer, as the gunfire rang and echoed. Cas couldn’t think and was too shocked and scared to move. Dean was trying to shield Cas as best as he could while shooting. Cas was staying low to the ground and wishing he had been able to just stay home safe with Dean. Benny must have rolled somewhere else because he wasn’t with them. There was swearing and yelling from both sides that was making the noise level overwhelming. 

To add to the cacophony of sound, police sirens started to wail.

 _Thank God they’re here_ , Cas thought for once in his life about the cops. 

“Dean, we’re going to be okay,” Cas said, so quiet he didn’t even know if Dean heard him. But he needed to say it anyways, even if just for himself. “Dean?”

Cas got up into a kneeling position as they gunfire lessened and the sirens got louder. He could hear an abundance of footsteps as guys from both side headed to the nearest door to avoid the cops.

The only sound now was the police sirens from outside.

“Fuck, Cas,” Dean winced. His eyes were closed.

“Dean, what’s wrong?” Cas said, forgetting about everything else. Dean was holding his chest near his collarbone and when he pulled it away, there was blood. A lot of blood. He’d been shot.

“DEAN!” Cas yelled. “Dean, stay with me, keep your eyes open, damn it!” 

The cops had finally come in. Cas saw Henriksen first.

“Henriksen, call an ambulance, please,” Cas begged. 

Henriksen did as Mills rushed over to help apply pressure to Dean’s shoulder. Dean’s eyes fluttered open, meeting Cas’s. 

“Cas…”

“I’m here, you’re going to be fine Dean,” Cas whispered. Dean had fallen back onto Cas’s lap and his eyes closed again. 

 

Paramedics rushed into the warehouse after the eternity it felt like it took them to get there. Henriksen quickly directed them from the front door to where Dean was lying unconscious on Castiel, still bleeding profusely. Cas didn’t want to let go of Dean but he had to let them take him. 

He blindly followed the stretcher carrying Dean out the door and towards the waiting ambulance. As he walked, he couldn’t help but think this had to be a dream. How could this be his life? The boy he fell for was in a gang and now had been shot. It didn’t feel real. 

Cas was all set to get in the ambulance and go with Dean to the hospital, had every intention of staying by Dean’s side until he knew he was okay, but was stopped.

Mills put a hand on his shoulder. Cas tensed up. Did she really want to mess with him right now? There was no way he wasn’t going in that ambulance.

“Castiel, you have to come with us,” she said, low so only he could hear it, “you can’t blow your cover.”

“I don’t care, I’m going with Dean,” Cas said in a low, dangerous voice. Just as dangerous was what he was willing to do in that moment to make sure he was with Dean, holding his hand. Police or not, he would fight anyone who stopped him.

“No, you’re not,” Henriksen stepped beside Cas. “You heard her, you can’t…”

“Screw you! I don’t care!” Cas yelled, not caring about his damn cover. Dean, _his_ Dean, was in an ambulance, had been _shot_ and these two were telling him he couldn’t go with him? It was bullshit and Cas just wanted to be with Dean. 

He made a feeble attempt to run to the ambulance before it drove away. Henriksen grabbed him around the middle and Mills put both hands on his shoulders to push him back. Henriksen handcuffed him and half-dragged him to the squad car. He kept fighting them both until the ambulance doors closed and it started to drive away. He let out a breath and all of the fight left in him went with it.

That’s when Cas began to cry. Cried for Dean, for himself, the shitty situation he had gotten himself into and the general _suck_ that had been his life. The suck that had existed until he had met Dean. And now he might be taken away from him, too. 

Cas had been oblivious to anything besides Dean until that point and he now looked around through blurry, tearful eyes as he was roughly loaded into the squad car by Henriksen. Crowley and Dick had been grabbed as well as a couple of guys from Michael’s gang, Uriel and the blonde one with his usual black V-neck, or at least that’s what Cas remembered him in from last time. 

Crowley had an initial look of disbelief but then attempted to look expressionless. Hopefully, Mills was right and Crowley would continue to believe Castiel wasn’t working with the police. It was generally impossible to tell what Crowley was thinking or scheming. 

The ride, while short, was excruciating. The entire car ride for Cas was full of almost every memory he had of Dean.They needed to hurry so Castiel could run to Dean at the hospital. Considering his lack of a car, that would probably be literal. 

Cas never told him he loved him, told him _why_ he loved him. How he was with Sam, the soft side under his bad boy exterior, his passion for cars, the way he looked at him with what could only be love too…

 _What if you never get to?_ whispered the sinister part of Cas’s brain. He squinted his eyes shut, hard, and tried to block that thought out as tears continued to stream down his face. Thinking like that wouldn’t help.

They got to the station and Castiel sat down in the interrogation room. It was cold and bare, which wasn’t helping Cas’s mood. He quickly wiped the tears from his face and tried to pull himself together to get out of there as soon as possible. There would be questions and as soon as Cas answered them, the sooner he could go. 

“We’re sorry about what happened…”Henriksen started to say.

“No, you’re not,” Cas interrupted, glaring at him. “I’m surprised you showed at all.”

“I get you’re upset…” Mills tried but Cas cut her off, too.

“You think?” he snapped. He almost felt bad seeing the hurt cross her face, he never had a problem with her and still didn’t, but he couldn’t bring himself to care. “How’d you know we were there, anyways?”

“GPS on your phone,” Henriksen answered like that was obvious. 

If Cas had been thinking clearly, it would have been. Also, he would have been pissed but he was too upset about everything else at the moment to bring himself to care about that.

“We didn’t get a chance to see the supplier. Did you get a name?” Mills asked, treading gently. 

“Yes,” Cas sighed, “Lucifer.”

“Was that his real name or a street name?” Henriksen asked, almost smirking, which pissed Cas off. 

“How the fuck would I know? Everyone started shooting before I could ask him,” Cas retorted, shocking himself. 

Sure, he’d been upset and short with these two before but he never would have talked like that to a cop quite like that before meeting Dean. He looked down at his still handcuffed hands in his lap.

“Can I go now?” Cas asked quietly. He needed to get to Dean and he needed to go before he said something he’d regret because he was upset. 

Mills unlocked the handcuffs and let him go.

 

Outside the precinct, Cas smelled cigarette smoke and immediately thought of Dean and the way he always smelled like it. The smell would always remind him of Dean now. He turned to his left and saw the black V-neck wearing gang member from Michael’s crew smoking and froze, anticipating a fight.

“Whoa, easy,” the blond said, dramatically throwing his hands in the air, “I’m just glad to be out of there,” he gestured with his head towards the station, “I don’t want any trouble.”

“Same,” Cas agreed. He paused, looking left and right to try and pick which way was quickest to the hospital.

“What are you looking for, your guys aren’t coming right?” the guy asked, puffing his smoke. 

Cas shook his head. They weren’t exactly Cas’s guys anyway but this man didn’t need to know that. He almost asked about the guy’s accent that seemed British but didn’t care enough.

“Thinking of how to get to the hospital, not that it’s any of your concern,” Cas said.

“I was about to head over myself. One of your guys hit at the warehouse?” he asked, stomping out his cigarette. Cas nodded. “Need a lift?” 

Cas figured it was a bad idea, a trap maybe, but that was the fastest way to Dean so he didn’t care.

“Sure. Thanks,” Cas said, feeling the tension in his face, shoulders and everywhere melt just a little. He was going to be by Dean’s side.

“Balthazar,” the man said, extending a hand. Cas rethought what he was about to do for a split second before deciding a course of action. 

“Cas,” Cas said, shaking it.

Castiel threw caution to the wind and got in the car with Balthazar. The risk was worth it if he could get to Dean, he reasoned, and he needed to get there _now_. Talking to the police already wasted too much time. 

“So, Cas,” Balthazar said casually as he drove, “Which one of your boys got shot?” 

Cas’s first response was disbelief. How could he be so cavalier about this situation? He must have been used to this which Cas found unfortunate and kind of sad. 

“Dean,” Cas said, glad he didn’t start crying again, “At least, I think that’s it, he was the only one I was paying attention to.”

Balthazar raised his eyebrows. “Dean, huh? Bummer.”

“You don’t sound like you think it was a bummer,” Cas observed, wishing he would drive faster. 

“Well…”

“Look, I get it, you don’t like each other. But you don’t have to be an ass.”

“Hey, I’m driving you, aren’t I?” 

Cas couldn’t argue with that. They rode the rest of the way in silence. 

The unlikely pair arrived at the hospital and went to the front desk of the emergency area. 

“Can I help you?” the friendly nurse said.

“Yes, I’m looking for a patient, would have just come in with a gunshot wound, Dean Winchester?” Cas said in one breath.

“Are you family?” she asked with a smile. 

“Uh,” Cas paused but knew the answer to get in to see him, “Yeah, his…cousin.”

The nurse looked a little skeptical but nodded and told him she would page a doctor to come talk to him. He waited with Balthazar as she did.

“Are you looking for Mr. Winchester?” a tall doctor with shoulder length brown hair came up and asked. Cas couldn’t help but notice the doctor was wearing cowboy boots. Balthazar backed off to give them some space.

“Yes, where is he?” Cas demanded, turning on the doctor who took a step back.

“Take it easy,” the doctor said. “He just went up to surgery, the bullet hit an artery.”

Cas let out a deep breath and closed his eyes. 

“Is he going to be okay?” he asked with his eyes still closed. 

“It’s hard to tell,” the doctor said, “the blood loss alone…”

Before Cas knew what he was doing, he grabbed the doctor by the shoulders and slammed him into the wall.

“You _have_ to save him, that’s your JOB!” Cas yelled. 

The doctor shoved him off and said nothing as he stormed off down the hallway, smoothing his hair down as his boots clicked on the linoleum. Cas leaned against the wall and slid down. There were no tears because he felt too empty. His head was resting on his knees. 

_Shit_ , he thought, head snapping up, _Sam doesn’t know_. He had been too busy with the cops and worrying that he didn’t even think. He had to tell Sam what had happened. 

Cas threw his head back, purposefully hitting the wall hard. He pulled his phone out of his pocket. Castiel took a deep breath and let it out shakily before dialing.

“Hello?” Sam answered.

“Sam, it’s Cas.”

“Cas, is everything… _Ruby, shut up_ … is everything okay?” Sam asked. 

Cas’s stomach sank, knowing full well Ruby was bad for Sam. There was a more pressing issue at hand and Dean could talk to him about it later when he was okay. 

“Um, no…”

“Cas, what’s wrong?” Sam said fearfully. 

“Dean…got shot. I’m at the hospital now,” Cas said, the pressure from holding tears in too much and a couple fell down his cheeks. 

“Shit, really? Oh my God, okay. Okay, I’m coming. Thanks, Cas,” Sam hung up before Cas could answer. 

Castiel pulled himself up off the floor.

“How’s Dean?” Balthazar asked, coming very close to genuine concern.

“In surgery. How’s…who are you here for?” Cas asked, a little guilty he didn’t ask before considering he was nice enough to drive him. 

“Adam, he’s new. I told Michael to stay out of the high school and leave them alone but he didn’t listen,” Balthazar said remorsefully. “Now, I’m the only one here. Quite the surprise that I’m the nice guy.”

Cas was horrified that Michael recruited out of the high school and now one of them was in the emergency room. He was just a kid and didn’t even graduate high school. They sat, both just waiting, in the gut-wrenching waiting room. It was sterile, depressing and empty besides the two of them or so Cas thought. 

“Isn’t this a sight,” a voice drawled, sending a chill down Cas’s spine. Cas turned to his left and found the source of the voice.

“Crowley, really not a good time,” Cas snapped. “Why’d the police let you go?”

“I never actually did anything wrong, Lucifer made sure of that, and the police don’t care if we shoot each other. It makes their job easier. Why’d they let you go?”

Cas stood up to face him. “I didn’t shoot at anyone.”

“You tell them everything you know?” 

“I didn’t tell them anything,” Castiel growled, “You should go.”

Crowley seemed to ponder fighting then decided against making a scene in a hospital waiting room. It seemed like, for now, he believed Cas.

“Tell your boyfriend,” Crowley paused and Cas tensed up, which caused Crowley to smirk, “I stopped by.”

“Fuck,” Cas said, sitting back down after Crowley left. 

“Is he really your boyfriend?” Balthazar asked with a slight grin.

Cas just turned and gave him a look. Balthazar shrugged. 

A doctor came through the doors leading to the rooms, a different one than Cas encountered earlier. 

“Are either of you here with Adam Milligan?” she asked. 

“Yeah, I am. What’s the news, doc?” Balthazar answered. 

“He, um… I’m afraid I have some bad news. Adam is dead,” the doctor said with remorse. 

“Damn it,” Balthazar cursed, “Well, thanks for telling me, I guess.” 

The doctor nodded grimly and left through the doors she came in through. 

“Well, I guess I’m done here,” Balthazar said, “gotta go tell the guys. See ya around, Cas.”

Cas nodded and Balthazar left. Almost right after he did, Sam showed up. 

“Cas, what happened?”

“We were in a warehouse and they were shooting at us…”

“A warehouse? Who’s they?” Sam asked, obviously confused.

“Sam…” Cas was going to say he couldn’t really explain it when the doctor Cas talked to outside of Dean’s empty room returned. He seemed wary of Cas and eyed him with caution. 

“Are you both here for Dean?” the doctor asked, noticing Sam. 

“Yeah, I’m his brother, is he okay?” Sam replied. “Please tell me he’s okay.”

“They’re bringing him down from his surgery, you can visit him after he wakes up,” the doctor said before leaving.

“Oh, thank God,” Sam said as he collapsed back into his chair in the waiting room.

Castiel let out a huge sigh of relief and sat down as well. He closed his eyes and kept thinking, _He’s fine, everything’s going to be fine…_ At least, Dean was going to be. Everything else would have to wait. 

“Cas, you have to tell me what happened,” Sam said. He shifted his body to face Cas. 

“I can’t, Sam,” Cas replied, also turning in his chair. It was hard to look Sam in the eye because he was using what Dean called his “puppy dog” eyes. They were hard to resist.

“Why the hell not? My brother just got shot, I think I deserve to know what’s going on.”

“I know it’s hard right now but…”

“Don’t talk to me like I’m a freaking child!” Sam interrupted, his voice getting louder. One of the nurses turned her head with a disapproving look. 

“Dean’s just looking out for you,” Cas said, his voice somehow still calm. 

“Yeah,” Sam scoffed, “he thinks he is.”

“He’s protecting you,” Cas defended and Sam scoffed again. “I’m serious, Sam. It’s the same reason he told you to stay away from Ruby.”

Sam had a look of mixed shock, hurt and anger.

“You…you have no right…” he sputtered, “It’s none of your business who I hang out with! Dean’s either.” 

“He…”

“Don’t you think you might have a biased opinion, considering he’s your boyfriend? Just stop talking, Cas.”

Cas shut his mouth and they sat in a pretty uncomfortable silence. Figuring no news was good news right now, he didn’t mind waiting out here until Dean woke up but the tension was eating at him. How could Sam not see where they were coming from? Sam could stay in blissful ignorance, focus on school, date Jessica, to be a normal kid. Cas knew that was all that Dean wanted, was for Sam to be happy and normal. And if Dean was happy, Cas was happy so he wanted that, too. 

After what felt like half a day ticking away, the doctor returned an hour after Sam got there to let them know Dean had woken up. 

Sam and Cas followed the doctor, his cowboy boots clacking on the white linoleum. Dean was laying in the hospital bed in one of those awful gowns, a mint green one. He had an IV drip in his arm and chords to a heart monitor disappearing under the garment. Some of the bandaging from the wound was visible and his arm was in a sling. 

“Cas,” Dean said, his voice hoarse. He still seemed very groggy from the anesthesia. 

Castiel sat next on the right side of Dean’s hospital bed in the plastic chair and held his hand. “Hello, Dean.”

“Is Sam… where’s Sammy?” Dean asked, brow furrowed. 

“I’m right here, Dean. How are you feeling?” Sam said, standing on the left side of the bed. Dean’s eyes slowly found him.

“How the hell you think? I’ve been shot, bitch,” Dean said, before starting to cough.

“Not an excuse to be a jerk,” Sam said before getting Dean a cup of water. Dean let go of Cas’s hand briefly to drink the water before lacing their fingers together again. 

“Did you meet my doctor? I’m calling him Doctor Sexy,” Dean smiled at Cas, kind of out of it and a little loopy. Cas just laughed and shook his head. 

“Isn’t this touching,” a voice said at the door. Three pairs of eyes snapped to the room’s entrance to find a couple of police officers there.

“Henriksen, what do you want?” Dean snapped. The slight slur from exhaustion took a little away from the usual bite in his tone.

“I wanted to bring you flowers,” Henriksen joked. Dean rolled his eyes. 

“If you didn’t hear, Adam Milligan is dead,” Officer Mills said. 

“I heard,” Cas said at the same time that Dean and Sam said, “Who?”

“One of Michael’s guys,” Henriksen explained. “So now, this is becoming a full blown investigation. Where’s your gun, Dean?”

“My what? I don’t own a gun!” Dean feigned. 

Sam looked startled and looked like he wanted to say something really badly or ask a million questions. 

“Don’t play dumb. Your gun. We need to check it out,” Henriksen said snidely. 

“I don’t have one,” Dean insisted. 

Cas didn’t see it in the room and assumed it got left behind at the warehouse. Cas knew that Dean wasn’t really looking when he had been firing his gun in the firefight and Cas shuddered to think that Dean might have accidentally hit the kid. That would be a concern for another time. He needed to heal and get better now. 

“All right, we’ll let you rest. But we’ll be back with a warrant,” Mills said, leading Henriksen out of the room with a hand on his shoulder. Dean let out a deep breath and Cas squeezed his hand. 

“Dean…” Sam began, “Do you have a gun? Who’s Michael?”

“Aw, come on, Sammy, you heard the cop. Let me rest,” Dean said, closing his eyes. Sam glared but decided Dean was right and left the room, giving them time to themselves.

“Oh, good, he’s gone,” Dean said, peeking open one eye to check the room. He opened the other looked at Cas. Cas got out of the chair to lean over Dean and give him a gentle kiss. His lips were a little dry but otherwise unaffected by everything that had happened. 

“Dean,” Cas sighed against Dean’s lips. “I was so scared. You need to stop doing that.”

“What?” Dean smirked.

“Almost dying,” Cas replied.

“I can try,” Dean answered, still smirking.

“You should rest.”

Dean pouted. Cas laughed and kissed him again, quickly. 

“You’re killing me,” Dean groaned as Cas sat back down. 

“Go to sleep,” Cas instructed. Dean raised his eyebrows. “Please?” 

“Love when you get all commanding,” Dean said, closing his eyes with a smile on his lips. 

Cas squeezed his hand again before leaning over on the bed to fall asleep as well, still holding Dean’s hand. Forget the cops and their investigation, all that mattered was that Dean was okay. 

 

~~~

 

Dean was released from the hospital two days later and when he was home, the healing process was fairly quick, or at least Dean pretended it was, since the bullet went almost clean through Dean. He stopped wearing the sling sooner than he should have as per Doctor Sexy’s orders and always insisted he didn’t need Cas or Sam’s help, which was crap. So they both did little things to make it easier for him without him knowing. 

Cas ran into Balthazar on the street not too long after, luckily without Dean who would shoot first and ask questions later, and asked how their gang was taking Adam’s death.

“Went over like a ton of bricks,” Balthazar had explained, “Those guys cared about him, or pretended to. Michael even seemed a little upset. The one who actually recruited him, Zachariah, couldn’t care less but that’s because he’s a prick.” The two parted ways after their brief discussion before either of them were spotted by any gang member of either side. 

Crowley made sure to still receive their shipment from Lucifer despite the stunt he pulled. He just kept it a one on one meeting and had Dick and Edgar tail Michael long enough to make sure their gang wouldn’t show and cause trouble. This allowed the boys to continue to sell like usual. In hopes of keeping Crowley away from Sam, Dean returned to selling when his gunshot wound healed. Crowley was decent enough to allow him a little time off which was a nice surprise. 

 

~~~

 

It was late September and Benny was getting closer and closer to his wedding to Andrea. He seemed ridiculously stressed, more so than Cas had ever seen him in the short time he knew him, and Dean and Cas allowed him to skip selling and still get a cut to try to help him. Because Crowley valued Dean more and wasn’t worried about Benny’s significant other being a snitch, it didn’t matter to him that Benny would occasionally not be on their corner. 

Shockingly, Mills and Henriksen had been maintaining radio silence since the warehouse firefight. They hadn’t visited about the gun, which Dean thankfully found hidden in the maze of boxes in the warehouse after the cops searched it. The police didn’t mention who they believed killed Adam Milligan either. It was like waiting for a scorpion to strike out and sting and it was unsettling. 

On the last Saturday in September, Dean and Cas returned to Dean’s thankfully empty apartment after selling and going for drinks at the Roadhouse. Dean had more than he had in a while so Cas, having had only one beer, drove them home in the Impala and had to keep pushing Dean off of him. A little bit of booze and he got really handsy. 

After pressing Cas against the closed front door and kissing him, hard, Dean stopped and smiled teasingly at Cas. 

“Fuck, why are you stopping?” Cas moaned, wanting Dean’s hands on him again and the taste of whiskey from his mouth. Dean kept smiling and headed into the small kitchen area and returned with a full bottle of what Cas guessed was more whiskey. He opened it and took a long pull and Cas was mesmerized by his mouth as he did. Dean led Cas with his other hand to the couch.

“Cas,” Dean pleaded as they both sat, “drink some.” 

“Dean, come on,” Cas protested. 

Cas had still never been drunk with Dean and usually only had a few beers at most when he drank. He just didn’t see the point. But Dean just looked at him with his beautiful eyes and freckles and full lips and…

_Shit._

“Fine,” Cas agreed, unable to say no to Dean. 

He took the bottle with slightly more force than necessary and took a small shot. Since he hadn’t taken a shot in a while, he coughed and sputtered after. He and alcohol really didn’t mix well. Dean laughed, loudly.

“Shut up,” Cas wheezed, trying to pull himself together. Dean took the bottle again and drank, clearly better at drinking than Cas. 

“Get at my level,” Dean joked. 

Cas took another shot and this one went down a lot more smoothly. 

They continued to make out on the couch, Cas on top, and occasionally took a break to drink more. Cas was taking the lead, moving his hips against Dean and gently biting his lower lip while being careful of his still healing bullet wound. When half the bottle was gone, Cas decided he had enough.

“I think I’m starting to feel something,” Cas hiccupped, making Dean laugh. He went to drink more but was crazy drunk and Cas put the bottle back on the coffee table and kissed Dean. They were both half-hard and Cas was about to suggest they move to Dean’s room.

They were interrupted by Sam who stumbled through the front door. Cas jumped off of Dean and immediately regretted moving so fast so quick as it did his stomach no favors. 

Dean stood up slowly to confront an intoxicated Sam. 

“Wha… what the shit, Sam, Sammy, are you _*hic*_ drunk?” Dean mumbled, swaying where he stood. Cas stayed on the couch where he tried to control his stomach and stay out of the family spat.

“The fuck, look who’s… who’s talking,” Sam slurred as he shut the front door. 

“Well, yeah, but I’m older. You, you can barely drive!” Dean argued. Sam rolled his eyes.

Dean paused and inhaled, deeply. Cas couldn’t see his face but he guessed he was narrowing his eyes at what he smelled. 

“I swear, if that’s weed…”

“What’s it _*hic*_ to you? You smoke it too and, and you did when you were _*hic*_ my age,” Sam paused to burp, “Hell, Dean, you fucking SELL it!”

Dean froze up. 

“Fucking Ruby,” Dean muttered under his breath, knowing she must have told Sam. He didn’t know how much she said but that was enough. Cas still didn’t know whether or not to interfere.

“Screw you, she has… nothing to do _*hic*_ with this,” Sam argued, leaning on the kitchen counter. 

“Right,” Dean said. Cas could hear the eye roll. “I said she was bad news.”

“And I said screw you,” Sam spat back. 

He headed uneasily towards his bedroom. Dean grabbed his arm as he walked past and Sam pushed him off. Dean’s balance was off from drinking and he fell, landing on his bad shoulder.

“God damn it,” Dean cursed, eyes shut in pain. 

Sam stopped by his door and he seemed to be on the brink of apologizing for causing Dean to fall. Cas, who had been silent, finally got into action. He got on his knees on the floor next to Dean. Cas hadn’t seen a domestic argument this bad in years and wasn’t sure what to do. Any other type of conversation and Cas would have been laughing at the two brothers trying to talk with drunk hiccups but this was far from humorous. Cas had never seen the two of them like this before.

“I’m fine, I’m fine,” Dean said, allowing Cas to help him only in the slightest to get up. “Sam, we’re not done!”

“Yes, we are,” Sam shot back, opening his bedroom door.

“Sam, get the fuck back here,” Dean ordered. 

“YOU’RE NOT DAD!” Sam screamed before slamming the door shut. 

It shook the whole apartment and made Cas’s ears ring. Dean sat back on the couch, looking exhausted. Cas joined him. Dean reached for the bottle.

“Dean, I think…” Cas tried, a little concerned.

“Cas, please,” Dean begged. Cas caved and without looking at Cas, Dean drank. 

“Do you want to…”

“Not at all. I want to sleep,” Dean answered. He set the bottle down.

Cas followed Dean into his bedroom. They changed into comfier clothes and climbed into bed. 

For a change, Dean was the little spoon and curled into Cas and pressed his back to Cas’s chest. Cas held him tight. It was nice to hold and comfort his boyfriend. Dean was allowing himself to be a little bit vulnerable and Cas would take it while he could. 

“I’m sorry you had to see that,” Dean said slowly. 

“It’s okay,” Cas said understandingly, “families fight.”

“Nah me n’ Sam,” Dean slurred, his tiredness and intoxication making him hard to understand. Also, Cas was listening through an alcohol-sloshed brain. “We don’t…didn’t. Always a _*hic*_ team against…” 

His voice trailed off but Cas was curious what he meant.

“Team…against what?” Cas asked. 

“Everything.” Dean said, “But our dad, mostly.”

Cas was going to answer but Dean continued.

“Can we sleep?”

Cas nodded against Dean’s shoulder and neck, breathing in the unmistakable scent that was pure Dean. There was a faint smell of cigarettes and whiskey and his body wash. Cas never figured out what the scent was exactly but he knew he liked it. 

“Thanks, Cas. For…being you,” Dean stumbled. 

“You’re welcome, Dean,” Cas said, smiling a little. His cheeks got warm, adding to the heat the alcohol provided there already.

“I l…” Dean yawned. Cas waited. 

“Lo…” Dean seemed to forget what he was trying to say. “You.”

That was the last word before his breathing slowed and Cas felt his heartbeat slowing down under his arm. It was pretty sobering and Cas found it hard to sleep until the alcohol won and slowly dragged him down. 

Any other night, he wouldn’t have gotten any sleep because his drunk boyfriend seemed to try to say, “I love you.”


	9. Chapter 9

The next morning, Cas woke up with a headache and the warmth of Dean pressed to his front. Cas usually didn’t drink because he always managed to be at least a little hungover the following day and got an upset stomach. He nuzzled his face into Dean’s neck, breathed him in, and ran a hand slowly up his side, ghosting his fingertips along to ease him awake.

“Cas,” Dean mumbled into his pillow, “fff mo’ min…”

“What?” Cas asked in his ear. Dean moved his head just a little to get his face out of his pillow to talk. 

“Five more minutes,” Dean muttered, eyes still closed, “My head fucking hurts.”

“I’m sorry but we both have work. Up.”

Dean turned his head back to kiss Cas. It started short and sweet, but Cas quickly deepened the kiss and snuck his tongue into Dean’s mouth who had turned to face Cas.

“Good morning to you, too,” Dean laughed when they stopped to breathe after a few minutes. “I think I found the cure to a hangover.” He kissed Cas again. 

The two got up and got dressed before brushing their teeth. As Castiel brushed, he thought about what Dean almost said last night. He was drunk and almost asleep so he probably didn’t mean to say it. Considering he didn’t bring it up this morning, although Cas didn’t expect him to, he must not remember it. But the fact that any version of Dean was close to saying “I love you” made Cas ecstatic. The conversation about it, if they ever had one, could wait. Cas really did need to get going. 

Cas headed to the kitchen and made coffee while Dean stood in front of Sam’s door, poised to knock. It was clear that Dean was struggling whether to knock or not after their fight last night.

“Sam? I’m going to work,” Dean called. He paused, shooting Cas a concerned look who shrugged. 

“SAM!” Dean called again, louder. He opened the door and looked in. “What the fuck… he’s gone!”

“Look, don’t worry, he probably just went to study or hang with Jessica or something,” Cas reasoned, trying to make him feel better. It was what Cas hoped for Sam, anyways. 

“It’s my job to worry about that kid, especially if he’s getting drunk and smoking weed,” Dean pointed out, walking into the kitchen area. 

“Just have some coffee…”

“I don’t want coffee,” Dean snapped. 

Cas glared back at him. Understandably, Dean was upset but he didn’t have to take it out on Cas. That wouldn’t get Sam back. This was not the time to argue.

“I get that you…” Cas started, keeping his voice level.

“No, you _don’t_ get it Cas,” Dean said, looking right at Cas. They were standing a foot apart, glaring at each other. “I have to look out for him, keep him safe. He’s my little brother.”

Cas didn’t want Dean to snap at him again so he said nothing, just kept his mouth in a straight line. He really didn’t want to fight with Dean.

“I need to find him,” Dean said, sounding slightly defeated and looking down. “He’s the only family I have.”

Cas tried to not to feel hurt that Dean only felt close to Sam. Without Sam, he still had him, his boyfriend. Maybe it wasn’t exactly family but it was something. Even if they didn’t say it yet, they loved each other. Cas understood that the two brothers were really close, definitely closer than he and Gabriel were. It wasn’t fair to only focus on that relationship in his life when he had Cas, a dedicated boyfriend who was willing to help in whatever way Dean needed him to.

“I know,” Cas said, then looked at the clock in the living room, glad for an excuse to go. He didn’t want to say something he’d regret and had to get out of there. “And we will find him but I have to go.”

“Yeah,” Dean said, still distracted, “I’ll, uh, see you later then.”

The awkward tension that filled the air was almost suffocating. Cas nodded at Dean and left. 

At work, Castiel could barely focus. He was too worried about Sam and went back and forth between angry with Dean and worried about him, too. 

 

Dean spent Sunday under the hoods of several cars, getting good and dirty until it was quitting time. It was a small help to clear his head for a little bit at a time. Cars were easy to understand and sometimes Dean preferred them to people. It was a problem to solve and then another came along and it was simple to Dean. They made sense to him. 

When he got home, still no sign of Sam and Cas hadn’t called or texted. He ignored the other stuff on his phone from Benny and grabbed a beer and sat on his couch. The TV was on until he just fell asleep on the couch waiting for Sam who never showed. 

The next morning, Dean called the school’s attendance office and the secretary let him know that Sam was there which was a small relief. 

_Oh, good, Ruby didn’t get him killed,_ Dean thought bitterly. When Sam still never showed up to their apartment, at least while Dean was there, Dean decided to go have a chat with Crowley. 

Dean drove over to Crowley’s house and knocked on the door. Thankfully, he was home. 

“Dean,” Crowley smirked, wearing only a black robe, “What can I do for you?”

“First, you can put on some real clothes,” Dean retorted.

“Not happening,” Crowley responded. “Next?”

“You can tell Ruby to lay off my brother,” Dean demanded. 

“I only told her to drag your brother in while you weren’t selling. I wanted at least one Winchester paying the debt for that old drunk’s garage.”

“Watch it,” Dean growled, ready to pull his gun or punch Crowley or both. 

No one insulted Bobby Singer in front of Dean. Crowley put his hands up in a joking surrender. Dean put all of his effort into not punching his stupid, smug face.

“Anything Ruby is doing now is of her own accord. I only control the bitch to a point,” Crowley finished and went back inside, not letting Dean get a word in before he shut the door. 

Dean tried Sam’s cell, again, and it still went straight to voicemail. 

 

Tuesday went by and still no Sam. Dean sent a quick update to Cas and got only one word answers but he could only worry about so much at a time and Sam was the current priority. 

Wednesday morning, Dean again called the attendance office but this time, there was no Sam. The only place he could think of was Ruby’s. He had been once, a while back, for a party and still knew where it was. 

Dean drove there and marched right to the door of the shitty run-down house. It was close to the street, one story and what was probably once white in color. Cigarette butts and empty beer cans littered the lawn that was more dirt than grass. The door opened and behind it stood what looked to be an older version of Ruby, if she kept drinking, smoking and maybe took up meth. 

“Who the hell are you?” the woman spat in a raspy voice, drinking a beer despite it being nine in the morning.

“Mom, it’s fine, he’s a friend,” Ruby said, coming out of nowhere. 

Her mom grumbled into her beer and walked away. Ruby stepped on the concrete slab of a front stoop with Dean, closing the door behind her and crossing her arms.

“Well?” Dean asked.

“Well what?” Ruby answered.

“Well, where’s my brother? You’re not hiding him in this shithole are you?”

“Hey, don’t be an ass,” Ruby said. Dean sighed. It was mean to say but he wasn’t taking it back. 

“Is he here or not?” Dean asked, sticking to the point.

“Not,” Ruby replied. “Now go away.”

Her rough goodbye was fair considering Dean insulted her house and he left. Sam wasn’t here and any more time at the dump was a waste. He got out of there as quickly as he could.

 

Wednesday night was getting darker. Sam still hadn’t come home and Cas was still snippy in his replies. 

Dean was sitting on the couch, jiggling his leg absentmindedly and staring at his phone in his lap when the front door opened. 

“Sam!” Dean exclaimed as his little brother came home. He stood up. “Where the hell have you been? I’ve been worried sick! I called the school, they said you didn’t show today or yesterday!” 

“So?” Sam shrugged, not showing an ounce of concern.

“Are you kidding me? You’re the star student, on the fast track to Stanford. You’re going to get out of here, Sammy!”

“Don’t,” Sam rolled his eyes. 

“Don’t what?” Dean asked, confused what Sam could be talking about.

“Don’t lecture me about grades and college and shit, okay? I get it at school from the teachers who say I have ‘so much potential’ compared to everyone else and I got it from Dad. Just stop.”

“You have to be the Winchester that goes somewhere, man! You’re the only one who can.” 

“Why? Why do I have to? Don’t put your crap on me. Just leave me alone, I want to go to bed.”

Dean didn’t know what to say so he let Sam pass without a word. 

Since when did Sam change so much? Was it because of Ruby or was it before then? Had Dean been too caught up with Cas that he neglected his only brother, his only family?

Dean sat on the couch and picked up his phone. 

Dean: **Sam’s home**

Cas: **Glad to hear it.**

On top of the problem with Sam, Dean didn’t know what was going on with Cas. Everything was giving Dean a headache so he walked to the kitchen to grab a bottle of whiskey and went into his room. He drank until he wasn’t thinking about Cas or Sam or anything at all. 

 

Thursday morning was bright. Way too bright for Dean, who was unfortunately very hungover. He always hated himself the morning after drinking but he could always count on Sam to make him a nice, greasy breakfast. 

_Fuck_ , Dean thought, remembering that Sam had gone off the rails. His once caring and thoughtful brother was smoking weed and getting drunk with freaking Ruby. It might be hypocritical of Dean, who did that at sixteen too, but this was Sam and it was with Ruby. Sam was going places and Dean knew he never had the chance. He could pretend getting his GED with Cas made a difference but it was really a chance for Cas. Cas was smart, like Sam, and had gotten screwed by shitty situations in his life. Both of them would get to college if Dean had anything to do with it. 

Dean dragged himself out of bed and checked the apartment. No Sam. Making matters worse, his booze was now gone because of his own stupid, borderline alcoholism. He’d need to get more. 

_Fuck_ , Dean thought again. A few quick phone calls confirmed that Sam was not at school or with Ruby. Crowley had no idea either, but that wasn’t a shock. 

Dean went to Bobby, Ellen and Jo’s apartment, which was one floor under theirs. None of them had seen him anywhere recently, not in the building, the garage or the Roadhouse. Dean was grasping at straws and in a last ditch attempt, drove to Jessica’s house when school was out. He knew where it was from dropping Sam off before on his way to work. 

“Hey, Jess,” Dean greeted when she opened the door. When she saw him, she scowled. “No chance Sam’s here, is there?”

“No chance in hell,” Jess said angrily, “When you find his ass, tell him we’re through!” 

She slammed the door in Dean’s stunned face. 

_How far gone was Sam?_ Dean thought, the pit in stomach getting heavier. _How did he manage to mess this up?_ Jess seemed great and Sam had somehow ruined what they had. Dean really needed to find him before anything else shitty happened. 

 

“Hello?” Cas answered his cell. 

Dean called him as his last hope. Everyone else was busy with work or school or planning a wedding which left Dean to find his little brother, his one responsibility, alone. 

The number one of rule of protecting Sam had been pounded into his brain for so long that he said stupid shit to the guy he, in all honesty, was probably in love with. If only John knew that… 

Forget John, right now he needed Cas. Any crap with his dad was in the past and could wait. That realization about how he felt about Cas would need some further thought later but right now he needed to convince Cas to help him.

“Cas? Hey, man, it’s me, I need your help,” Dean said from the other line, nervous to hear Cas’s reaction. 

“Really,” Cas replied drily. That was kind of what Dean expected. 

“Look, I know I was an ass…”

“Understatement.”

“But, seriously, I need your help,” Dean pleaded. If Cas said no, there was no one else for Dean to turn to for help. 

“Why _my_ help?” Cas asked, knowing the several people Dean could go to instead, his _family_. Cas was bitter, sure, and he wasn’t going to sugarcoat that. 

“Because you’re the only one who will help me, okay?” Dean admitted. It felt kind of lonely to admit. 

“Fine,” Cas sighed. “I’ll come over.” He hung up before Dean could say anything. 

_This will be fun_ , Dean scoffed to himself. 

 

Cas showed up at Dean’s apartment door with his arms crossed. In a short period of time, Dean had seemed to almost say “I love you” and then practically ignored him while trying to find his brother. Cas only wanted Dean to appreciate that he was there for him, no matter what, and that he was especially there to lean on when shit hit the fan.

“Hello, Dean,” Cas said, but it was cold, lacking the usual warmth when Cas said Dean’s name. 

“Uh, hey, Cas,” Dean stammered, rubbing the back of his neck as he let Cas in and shut the door.

“So, I take it I’m here because Sam is missing again,” Cas guessed.

“Yeah, he was here last night but he left. He was being all sullen and shit, too,” Dean explained. 

Cas eyed the empty whiskey bottle on the kitchen counter with raised eyebrows but didn’t mention it. Picking a fight wouldn’t help find Sam. They had talked about Dean’s drinking once and Cas had changed the subject before it got to be a fight. 

“Where have you looked so far?” Cas asked, figuring if he was here, he could be useful. 

“Um, Crowley’s, Ruby’s, Jess’s, the garage, the Roadhouse… he didn’t go to school either,” Dean listed. 

“Is there any other possible place he would go?” Cas asked. The list Dean made felt pretty exhaustive but Cas didn’t know Sam like Dean did. There had to be somewhere else. 

“Maybe. Let me check his laptop in his room,” Dean said. 

In Sam’s room, there was a periodic table of the elements on the wall and pre-law books already on his bookshelf in hopes of being a Stanford-educated lawyer. It was smaller than Dean’s room and Cas had a hard time picturing Sam and Dean sharing it before John died and Dean took his room. It would have been ridiculously tight. 

Dean opened Sam’s laptop and attempted to log onto it. The picture for the log on screen was one of Sam and Jess. 

“You know his password?” Cas asked.

“No, but I can guess it,” Dean said. 

Soon enough, he was in and checking the browser history. Dean made a joke about Sam being so clean and prude but Cas just rolled his eyes. Dean cleared his throat and kept looking. Besides links obviously used for homework, there was a recent one that held the answer. 

There was purchase for a bus ticket from Chicago to Kansas City.

“Why Kansas City?” Cas asked, assuming that’s where Sam ran off to but it seemed random to him. 

“Because it’s next to Lawrence,” Dean explained. 

Cas remembered Dean saying it’s where his parents were from but Cas didn’t know what the connection would still be. 

“I was scared of this,” Dean said, dropping his head a little. 

“What?”

“Our grandparents still live there. He went to our grandparents,” Dean sat back in his chair. “We don’t even _like_ them.”

He ran both of his hands fitfully through his hair. 

“Oh,” Cas said. He didn’t even know Dean’s grandparents were still alive or why it would it be such a bad thing Sam went there. 

“Okay, this says it’s an eight hour drive and it’s already six so maybe stop somewhere a little over halfway…” Dean said, pulling up a map.

“Whoa, what?” Cas asked, taken aback. Dean was just going to up and drive to Kansas?

“Cas, I have to go get him,” Dean said point blank, finally meeting Cas’s eyes.

“Couldn’t you just call your grandparents?” Cas spit-balled. It seemed easier to get them to send Sam back then driving all the way to get him. 

Dean just laughed a little and Cas figured Dean _really_ didn’t want to talk to them so he wouldn’t ask about it. Yet. 

“Are you coming?” Dean asked, looking Cas in the eye with fierce determination.

Cas took a deep breath and let it out with his obvious answer. 

“Of course.”

Dean and Cas got into the Impala after Dean quickly packed an overnight bag and they headed to Cas’s apartment where he grabbed some stuff for the impromptu trip and left a note for Gabriel.

“So, are you going to tell me why you’ve been pissy all week?” Dean asked as they hit the road. 

“You really don’t know why?” Cas responded, a little shocked Dean was this oblivious. 

“No, that’s why I asked,” Dean rolled his eyes then kept them on the road. Cas looked at him in disbelief and then shook his head. 

“What?” Dean demanded, sparing a glance at Cas. 

“It will be a long car ride if we argue,” Cas said, trying to just drop it. 

“Yeah, well it will be longer if we just ignore whatever’s going on,” Dean pointed out. 

“Fine,” Cas agreed. 

“Fine,” Dean said. “So, what’s wrong?”

“You. _You_ are what’s wrong.”

“ _Me?_ What did I do?” Dean snapped.

“When Sam went missing on Sunday, you could have asked for help, my help, but instead you’d rather deal with it yourself until you have no choice but to ask me. You think you have to carry the weight of everything on your own and you don’t,” Cas explained. 

“You kind of just up and left on Sunday,” Dean said, trying to defend himself. 

“Well, you were kind of rude,” Cas argued. Dean opened his mouth and then closed it, realizing he was right. 

“So, this whole week…”

“I was basically waiting for you to finally ask for my help. I was there, Dean. I’m always there for you.”

Dean didn’t say anything but seemed a little more relaxed. 

“Also, I’ve been in foster homes with younger boys I felt were like little brothers to me,” Cas continued. “So, I do know what it’s like to take care of them.”

“Shit, Cas, I didn’t know,” Dean said, looking a little guilty.

“Well, I would have said it on Sunday if you hadn’t been in such a bad mood,” Cas pointed out. 

“I’m sorry for being an asshole this week, Cas,” Dean apologized. “I know you wanted to help and I should have been smart enough to come to you in the first place. But I didn’t want to drag you into this, you know? It’s a pretty fucked up situation.”

“I’m pretty familiar with shitty situations and this isn’t the worst thing ever. We’ll get Sam back and you can always count on me for help,” Cas said.

“Thanks, Cas. I mean, that’s what boyfriends are for, right? To help find missing little brothers?” 

Cas laughed and so did Dean who took the laugh as a sign that they were okay. 

They continued to drive, stopping only once for a bathroom break and so Dean could have a quick cigarette. Cas had forgiven Dean for being too wrapped in his family drama to bother with Cas. He understood how much Dean loved and cared for Sam and was glad he came with. 

When they were driving into Kansas City, where they planned to stay the night until moving onto Lawrence tomorrow, Dean brought up Benny’s wedding that was in two days. 

“I’m excited, I’ve never been a best man before. I didn’t think I would until Sammy’s wedding,” Dean admitted. 

“I’ve never been a groomsman, there aren’t many people who would invite me to their wedding let alone let me be in the wedding party,” Cas said, understanding where Dean was coming from. 

Castiel really only had Gabriel besides Dean and the idea of the wild Gabriel getting married was laughable so he wouldn’t be in that wedding party anytime soon. And the thought of being a groomsman and not the other groom at Dean’s wedding made Cas sick but he shook that thought away. It was too early for that kind of thinking.

 _Whoa,_ Cas thought, _where did_ that _come from?_ He hadn’t thought about them like that before. It must have been the upcoming wedding that made him think about his own future.

“Cas?” Dean said, snapping Cas out of it, “did you hear anything I said?

“I…no,” Cas said honestly, still a little thrown off by his own head, “I’m sorry, I was distracted.”

“It’s fine, I was just thinking… well, at weddings,” Dean said, clearly trying to spit something important out, “people usually have dates.”

“Right,” Cas stated. He hoped he knew where Dean was going with this but wanted to watch him squirm and actually say it. 

“But, we don’t really want people to know, um, about us so…”

“Dean, what are you saying?” Cas asked, not liking the ditch this conversation turned into.

“We shouldn’t go together, Cas, I mean we’ll be there together, but not _together _together, you know?” Dean stammered.__

__“What?” Cas snarled, angry again even though they worked out their previous issues._ _

__“You take Meg and I’ll go with Andrea’s friend, Lilith.”_ _

__“I don’t want to go with Meg. I want to go with you, my boyfriend.”_ _

__“Look, I want to go with you too but…”_ _

__“So, do it.”_ _

__“It’s not that easy,” Dean tried._ _

__“Actually, Dean, I’m pretty sure it is.”_ _

__“I can’t explain…”_ _

__“Try,” Cas demanded. Dean ran a hand through his hair, shot a nervous look at Cas, then white-knuckled the steering wheel and kept his eyes set focused on the road._ _

__“You know I like you, a lot,” Dean said, making Cas think he was off to a good start, “but the bad guys know it and the guys in our gang know it.”_ _

__“So?” Cas said, “Forget them.”_ _

__“I wish I could.”_ _

__“I don’t care about them, they don’t scare me.”_ _

__“Well, they scare me,” Dean said, pausing to let Cas take that in. “Do you realize how easy it was for Crowley to manipulate me into selling again by having Ruby hang out with Sam? What if they did something to you?”_ _

__“I wouldn’t let them and neither would you.”_ _

__Dean smiled a little. “I can’t let anything happen to you.”_ _

__“Like if I got mad and ran away to Kansas?” Cas snapped. It was a low blow and Dean’s mouth set hard in a straight line but Castiel was sick of Dean’s macho, white knight savior act._ _

__Dean didn’t say anything._ _

__“I can take care of myself and pretty soon, Sam will be able to, too. When are you going to look out for yourself, Dean? When are you going to realize there are people who care about you and who don’t want you sacrificing yourself?” Cas continued._ _

__“I guess never.”_ _

__“That’s stupid,” Cas said, brutally honest._ _

__“I was raised with one job, protect Sam. It’s who I am, I protect the people I care about.”_ _

__“Well, who protects you?”_ _

__“No one, I take care of myself,” Dean stated._ _

__“And you don’t see that as hypocritical?” Cas asked, glaring. Dean didn’t answer._ _

__They were silent as they drove up to the motel. Dean parked and walked to the office, not checking if Cas was following him._ _

__Dean was already talking to the desk clerk when Cas caught up, with enough time to hear the guy say the only rooms available were with just one queen bed._ _

__“Perfect,” Dean said sarcastically._ _

__They carried their duffel bags into the motel room and threw them on the cream carpeted floor by the door. Cas stayed by the door while Dean stood closer to the one bed. It had a hideous green and brown comforter on top of it. There was a bathroom, an old TV and a night stand on either side of the bed and that was about it._ _

__“You know, I can sleep on the floor if it’s such a big deal,” Castiel sassed, continuing their fight. Dean turned to face him, emerald eyes enraged and narrowed._ _

__“Oh, don’t be a drama queen,” Dean shot back, taking a step forward._ _

__“I’m not, I just figured if you can’t handle our relationship being out in the open, I guess you’re not mature enough to handle sharing one bed,” Cas continued, with a step forward of his own._ _

__“We’ve shared a bed enough times, you know I can,” Dean retorted._ _

__“Do you have any notion of how profoundly vexatious you can be?” Cas pointed out. He took another step forward and was in Dean’s face._ _

__“You realize simple words work too so I don’t need a fucking dictionary? You use such huge ass words when you get worked up,” Dean accused._ _

__“I do not!” Cas said, his voice getting a little louder. There was slight truth to what Dean was saying but there was no way Cas would admit it._ _

__“Yes, you do!” Dean yelled._ _

__“Just because you didn’t…” Cas trailed off._ _

__“Finish that sentence, I fucking dare you,” Dean growled. “Didn’t what? Finish high school, go to some prep school? Work in a damn library? So, I have a limited vocabulary?”_ _

__“That’s not what I was going to say,” Cas lied._ _

__“Look, why don’t you just shut the hell up?” Dean demanded._ _

__“Make me,” Cas retorted._ _

__His voice was low and rough and just what Dean liked. With a quick glance to Cas’s lips and back up to his eyes, Dean kissed Cas, roughly. He was pulling Cas back to the bed by his hips, slightly biting Cas’s bottom lip, making Cas moan._ _

__Dean turned them around and Cas kissed back just as hard as they fell back onto the bed, Dean on top. The mattress squeaked under them. Dean sat up above Cas as he straddled his hips to quickly rip off his shirt. He got rid of Cas’s just as fast and started to bite and suck Cas’s neck, making sure to leave harsh marks._ _

__Cas grabbed the hair at the back of Dean’s head and sharply moved him so he could kiss him again, working his tongue into his mouth. The fight and the lack of touch since Saturday fueled them, both of them hard and straining against their jeans. Forget how stupid the fights had been, they were worth it if this was the end result._ _

__Dean worked his hips against Cas to get some friction, anything, down there and Cas moaned into Dean’s mouth and moved his own hips up._ _

__“Cas,” Dean groaned against Cas’s neck, sucking and biting over the same bruises he just made on Cas’s neck. He cupped Cas over his jeans making Cas arch his back on the bed._ _

__“Fuck, Dean,” Cas breathed._ _

__“I told you to shut up,” Dean smirked, stopping his hips, hands and lips. Cas whimpered at the loss of Dean’s touch and movement._ _

__“And I told you to make me,” Cas challenged, enough to further spark Dean’s interest. Dean worked off their pants and boxers with desperation. He stopped to look at Cas, grabbing his wrists to pin them up by his head as he did so._ _

__“Fuck… so beautiful, Cas,” Dean said breathlessly, eyeing his boyfriend up and down. He moved his hips again, the lack of clothes making the friction more intense. A quick pause allowed Dean to grab the lube from his bag before returning over Cas._ _

__“Presumptuous much?” Cas asked, eyebrows raised. It seemed a little odd to bring those on a trip to retrieve your runaway brother._ _

__“I know you can’t resist me. And shush,” Dean joked. He set the condom aside and squirted some lube on his hand before taking both of their lengths in hand and moving up and down._ _

__Cas threw his head back with a loud groan that only made Dean move his hand quicker._ _

__“Dean,” Cas moaned, already close and Dean knew it._ _

__“Not yet,” Dean said. He wasn’t done with Cas yet. He slowed his hand down before letting go completely._ _

__“Well, that didn’t mean stop,” Cas complained._ _

__“Tell me what you want then,” Dean said suggestively._ _

__“I want you to ride me,” Cas breathed, thrilled to try something new._ _

__Dean smirked again, pleased with that answer. Cas took the lube to start opening Dean up for him._ _

__Their fight reminded Cas of their situation on how they met because of Henriksen and Mills’ plan and that if it works, Dean would go to jail. Cas felt awful and immediately tensed._ _

__“What’s wrong?” Dean asked._ _

__“Nothing,” Cas lied._ _

__Cas kept going until Dean was ready and then let him sink down on him. Dean raised up just a little before slamming back down._ _

__“Fuck, that feels amazing,” Dean groaned._ _

__Cas let Dean ride him, hard, until he was nearly yelling his name and coming inside him as Dean came untouched onto Cas’s stomach and chest._ _

__Cas hated that it was the most intense orgasm he’d ever had and the hardest he ever came because he hated lying to Dean but loving him at the same time. It was killing him. They cleaned up and Dean was asleep almost immediately while Cas tossed and turned, wracked with guilt._ _


	10. Chapter 10

The two of them woke up tangled together in the motel bed, still naked. It was early, about eight, but Dean said they should get going to Lawrence. He and Castiel showered then got their stuff to leave. 

They got into the Impala after Dean checked them out at the front office.

“So,” Dean said as he started the car and looked at Cas, “are we cool?”

“Yes, Dean,” Cas laughed. “After last night, I would say we are ‘cool.’”

The couple did seem fine, making their usual banter and just talking for the final forty-five minute leg of their journey to Sam and Dean’s grandparents’ house. 

As the car turned onto a quaint suburban road lined with identical houses and matching trees, Cas couldn’t help but laugh a little at the boring, cookie-cutter street. 

“What?” Dean asked, a slight smile pulling at the corners of his lips just from Cas’s laugh. He missed it while they had been fighting. 

“Nothing, it’s just so… not you. I can’t imagine if your parents had stayed here and you were stuck growing up in suburbia.”

Dean laughed at the ridiculous idea. 

It was difficult to think of him, Sam and their dad playing football on the lawn while his mom baked a pie but it wasn’t impossible. If they had stayed here, Mary wouldn’t have died and their dad wouldn’t have been sad or paranoid and it would have been, most of all, safe. Dean parked in the driveway of his grandparents’ two-story house as he thought maybe that life wouldn’t have been so bad. Maybe it would be good to escape the gang and the city and come here where people didn’t get shot and he didn’t have to sell drugs. Maybe Cas would come with him. 

Quickly shaking that last thought away, Dean and Cas got out of the car and walked up to the front door. Dean looked at Cas who gave him a reassuring nod and the strength to knock. 

An older guy, Cas guessed Dean’s grandfather, answered the door. He was mostly bald, just a little bit of silver hair above his ears, and gray scruff around the lower half of his face. His expression, if Castiel had to describe it, was a sour lemon look like everything displeased him.

“I thought I heard that old junker,” he said, his eyes shooting to the Impala in his driveway. “Come on in, I guess. Figured you’d show up.”

Dean set his mouth in a hard line and tensed but followed his grandfather inside. Cas was surprised Dean didn’t go off on the old man for insulting his baby but said nothing as he too went inside. 

They went into the cozy living room left of the front door. After Dean’s grandfather sat in an armchair, he motioned for them to sit as well.

“Samuel, where’s my brother?” Dean asked, getting right to it, as he sat on the couch. Cas joined him. 

“Upstairs, sleeping. It’s pretty early after all,” Samuel said. “You two must have had a long drive.” 

Samuel looked pointedly at Cas who Dean hadn’t had the opportunity to introduce.

“Oh, right. Samuel, this is Cas, my boyfriend. Cas, this is gramps.” 

“So, you’re fine with him knowing?” Cas hissed under his breath. 

Dean nudged him with his elbow in a “not now” gesture. 

“Boyfriend, huh? I could have guessed that from the…uh…” Samuel motioned on his own neck where Cas had bruises from Dean’s biting and sucking there last night. 

Cas didn’t bother trying to hide them but did blush a little. He almost forgot about those but they were a good memory, adding more heat to his warm face.

“Chalk that up to city living,” Samuel muttered distastefully. 

“What the hell is that sup…” Dean started but was interrupted by a woman who entered the room.

“Dean!” she exclaimed. She walked up with open arms and Dean stood to give her a slightly awkward hug, or at least Dean’s face conveyed that. 

“Hi,” he said. 

“And who’s this?” she asked, looking at Cas. He already like her more than Samuel. 

“My boyfriend, Cas,” Dean explained. 

“Boyfriend? Well, come here,” she opened her arms for another hug which Cas gave. “I’m Deanna.”

“Nice to meet you,” Cas said, noticing but not mentioning that Dean was obviously named after her. Deanna smiled warmly. 

“All right, we’re going to get Sam and go,” Dean said, determined. Deanna’s smile faltered.

“Yeah, like hell you are,” Samuel said, “he told us what happened!”

“Did he tell you I’m his legal guardian?” Dean replied, eyes narrowed. 

Samuel didn’t have a response to that. 

“So yeah, nice try but he’s coming with me,” Dean continued.

Before either Samuel or Deanna could react, Dean was heading up the stairs to find his brother. Cas stayed in the living room with Dean’s grandparents, figuring Dean needed to talk to Sam alone. 

Dean found the tiny room Sam was sleeping in and gently woke him up. Sam jumped awake from under a big plaid blanket and was very clearly shocked to see Dean.

“Dean?” Sam asked, rubbing sleep out of his eyes and sitting up. “What…How’d you find me?”

“There’s only so many places you could have gone and come on, it’s me. I’m an awesome older brother,” Dean grinned, sitting on the edge of the bed. 

Sam didn’t return the smile.

“Although, I don’t get why you chose here,” Dean continued. “We hate these two.”

“They’re our only other family. They were far away,” Sam shrugged.

“Whatever. Let’s go home,” Dean tried.

“You realize when someone leaves home they don’t want to be found right?”

“Sam…”

“Dean, you were acting like Dad and I freaked, okay?”

“Sam, I know. And I’m sorry,” Dean apologized. It used to be that being compared to his father was the highest compliment he could receive but that wasn’t the case anymore. “But you belong at home, with me. It’s you and me against the world, remember?”

“Not anymore,” Sam grumbled, trying to duck under the blanket. 

“What do you mean?” Dean asked, pulling the blanket back down. 

“You have Cas,” Sam said, sounding more tired than angry. Like he was giving up. 

“Well, you have Jess,” Dean countered.

“Probably not anymore,” Sam sighed. Dean didn’t have the heart to tell him what Jess told him, he wasn’t going to kick him while he was down. “I messed up, Dean.”

Sam looked up at Dean and looked more like a scared little kid than Dean had seen him look like in a long time, probably since their dad died. 

“It’ll be okay, Sammy,” Dean reassured. “We can fix this. Why don’t we head home? You can apologize to Jess and maybe the four of us can go on a double date, huh?”

“What about Ruby?” Sam asked in a small voice.

“Don’t worry about her,” Dean said, trying hard not to get irritated. She didn’t matter right now.

“I fell behind in school, Dean,” Sam said, looking down.

“And you’ll get back on track! If anyone can, it’s you,” Dean reassured. Sam looked back up.

“You think so?” 

“I know so,” Dean smiled. They stood up off of the bed and Dean pulled his brother into a hug.

“Glad to have you back, Sam,” Dean said when they stepped back. “Let’s go home.”

Downstairs, Dean and Sam’s return alleviated the awkwardness surrounding the trio Dean left behind. 

“We’re leaving,” Dean stated, leaving no room for debate. 

“Wait a minute,” Samuel said, standing up. He seemed to not pick up on Dean’s tone or just ignored it. 

“Look, thanks for looking out for me…” Sam started.

“But, you’ve done enough. We’re outta here,” Dean finished. 

“Why don’t you stay…” Deanna said.

“Stay? Here?” Dean laughed harshly. “After all we’ve been through, you think we need _your_ help?”

“Dean,” Samuel said warningly. 

“Where were you when Mom burned in a damn fire? When Dad died? I was seventeen and Sam was thirteen and our dad died on Christmas, Samuel, and we were on our own! Where were you then?” Dean said heatedly, years of anger flowing out. “You hated our dad, fine, but you left your own daughter’s children, your flesh and blood, on their own.” 

“We can help…” Deanna tried. 

“We don’t need your help. Not anymore,” Dean snapped. “Let’s go.”

Dean stormed out the door and Cas and Sam followed into the Impala. 

The ride home to Chicago included just one pit stop. The three of them parked at a rest stop in southern Illinois and Sam went to the bathroom. There were also a few picnic tables around but not much else. Dean and Cas decided to stay by the car and sat on the hood. Dean lit a cigarette. 

“Thanks for coming with, Cas,” Dean said as he exhaled.

“Of course, Dean,” Cas replied. There wasn’t anywhere he wouldn’t go with Dean, even when they were fighting like they had been. 

“No, really. I mean it,” Dean insisted, making sure to catch Cas’s eyes to convey his sincerity. 

“You’re welcome, Dean.”

“So tomorrow’s the big day,” Dean said, changing the subject. Feelings time was over. 

“Yes it is. I’m sure Benny’s excited,” Cas nodded. 

Getting married still seemed like an event that was so far away in his own life so Cas was having a difficult time trying to relate. Cas had never even been to a wedding before. Foster homes and juvie didn’t really make for a warm home environment where everyone got dressed up for something like this. 

“Yeah and nervous as hell,” Dean laughed. “I’ve only been to Bobby and Ellen’s wedding and it was really small.”

Dean took a few puffs of his cigarette, blowing the smoke away from Cas each time. 

“And look, I know it sucks we’re not going together…”

“I understand, Dean.”

“You do?” Dean asked, taken aback. He was almost expecting another argument. 

“I do. You’re trying to protect me and I get it,” Cas responded truthfully. “At the end of the day, you’re still my boyfriend.”

“Hmm, I like that,” Dean grinned, throwing his cigarette butt on the ground. 

Sure it would suck not going officially together but it wouldn’t be the worst thing ever. They would still technically be there together and could still have a good time.

“I like that, too,” Cas agreed. 

Dean scooted closer and pulled him in for a kiss. He still tasted like a cigarette but Cas didn’t mind. Cas had one hand on the back of Dean’s head and the other on the side of his face. Dean held Cas’s hip and the side of his face. They were starting to deepen the kiss when they were interrupted.

“Ew, gross,” Sam said as he walked back to the car. “Let’s go before you scar me forever.”

“How is this more scarring than when you heard us have sex?” Dean teased. Their faces were apart but hands still in place. 

“Don’t remind me, jackass,” Sam groaned with an eye roll. Dean laughed and they both hopped off of the hood. They all got in and back on the road, Cas riding shotgun. 

Cas sat close enough to Dean to whisper in his ear that he really liked making out with him on his car. Dean got a little pink and rubbed the back of his neck but didn’t answer because Sam was in the car. Cas laughed a little at Dean’s response and then slid over to put a seatbelt on. Sam shook his head in the backseat but with a slight smile. 

As he mentally patted himself on the back for getting Dean flustered, Cas’s phone buzzed in his pocket. He guessed it was Gabriel who might have still been worried even though he left a note because maybe he just didn’t see it.

It wasn’t Gabriel, it was a number he didn’t know.

Unknown: **Cas, we need to talk.**

Cas: **Who is this?**

Unknown: **Balthazar. Michael plans to crash Benny’s wedding.**

Cas: **Why?**

Balthazar: **Revenge for Adam’s death.**

Cas: **But he doesn’t know who killed him.**

Balthazar: **Not specifically so we’re going to target all of you. Michael doesn’t need a reason to attack you anyways.**

Cas: **Thanks for the heads up.**

Castiel continued to stare at his phone for a moment. This wasn’t good. How was he going to warn everyone? Cas didn’t suppose Crowley’s gang would take kindly to the fact that he got the information from one of their supposed enemies. They wouldn’t believe him either. 

“Everything okay?” Dean asked, interrupting his panicked thoughts.

“What? Yeah, why?” Cas answered, hoping he didn’t look as much like a deer in headlights as he felt. 

“Because you have a look that says everything isn’t okay,” Dean said matter-of-factly.

“Everything’s fine, just my brother asking when I’ll be home,” Cas lied. 

Lying to Dean made his stomach twist in guilt. Every lie was just adding up and when this tangled web was ripped apart, it was going to be a mess. 

 

Dean dropped Cas off at home with a goodbye kiss to thank him again and a promise to text or call later and that he’d see him tomorrow for the wedding. 

Cas went upstairs and threw his overnight bag in his room. 

“Gabriel?” Cas called out from his bedroom door. 

“In here,” Gabriel responded from somewhere in the apartment. 

“Hello, Gabriel,” Cas said, walking over to his room. Gabriel was sitting with his back against his headboard and reading a magazine. He lowered it when Cas came in. 

“How was the road trip?” 

“Fine,” Cas reported.

“So, the boy toy’s all good? Got his brother back?”

“His name is Dean. And yes.”

“Dean?” Gabriel asked, with raised eyebrows. 

“Yes. What about him?” Cas wondered what Gabriel’s sudden interest was all about. 

“Nothing,” Gabriel muttered, continuing to read his magazine. Cas ignored his brother’s weirdness and let him know he was leaving again and headed out. 

 

Castiel didn’t know who to tell about Michael and friends and their plan to ruin Benny’s wedding so he did what anyone would do when they were threatened. 

He’d tell the police. 

He walked to the station to talk to Henriksen and Mills. Luckily, they were there and not too busy. The three of them sat in their usual room and wasted no time getting down to it. 

“What’s this about, Castiel?” Mills began. Her voice was gentle and concerned, as always. 

“I got a text from someone in the other gang and he said Michael’s gang is planning on showing up at Benny’s wedding tomorrow,” Cas explained. 

“Why?” Henriksen yawned. 

“Retaliation for Adam’s death. I see you seem to be doing well with that investigation,” Cas sneered. 

There weren’t any recent developments in the case and now it seemed like it could come back to bite them in the ass. 

“Listen here you little…” Henriksen snarled, starting to get up. 

“So, clearly,” Mills cut him off and he sat back down, “you’re asking for our help.”

“Please. I don’t want anyone to get hurt.”

“We’ll make sure no one does,” Mills assured him. 

 

~~~

 

Saturday started out bright and beautiful. Castiel woke up after a fitful night’s sleep, tossing and turning worrying about a brawl, and was all ready to go to Benny’s wedding even if he was scared of what could happen. Unfortunately, it wasn’t for several more hours. He dozed in and out and listened to his music for a while before he got up at around noon and took a shower. 

Dean: **Are you ready?**

Cas smiled as he read the text. He couldn’t wait to see his boyfriend in a tux. 

Cas: **Yes.**

Dean: **Then I’m coming over now.**

Cas was glad for a little bit of alone time before they started their charade. Cas wasn’t looking forward to letting some girl be Dean’s date for the evening. 

Dean knocked on the door and Cas let him in, grinning ear-to-ear. He shut the door behind him. 

“Hey, Cas,” Dean greeted, a matching grin on his face.

“Hello, Dean,” Cas replied. 

“I had to come see you in a tux before anyone else,” Dean said. 

They took a moment to check each other out in their formal wear. Both of their rented tuxes fit great and the black bowties were tied perfectly. Shiny, black dress shoes completed each ensemble. 

“You look very handsome in a tuxedo, Dean,” Cas complimented, making Dean slightly red. 

“Thanks, Cas. You, uh… you too,” Dean stammered. 

Cas suggested they leave and led Dean out. 

 

After picking up their dates for the evening, the four of them went to the church. Lilith and Meg immediately got along and Dean figured that meant Lilith was bad news. It took a certain type of person to get along with Meg. 

“Thanks, Clarence,” Meg smirked at Cas.

“For what?” Cas replied. 

“Taking me as a date,” Meg rolled her eyes.

Cas nodded uncomfortably. He wished she didn’t use that word to describe their situation but that was the case, which sucked. 

Before the wedding, Dean did nice work to calm Benny down, ease his nerves and get him upstairs on time to start the ceremony. 

Benny stood by the priest at the end of the long aisle lined with pews. The stained glass windows with angels and saints on it let in an abundance of sunlight. 

Dean followed the flower girl and ring bearer, young cousins of Andrea’s who did a great job, with Lilith on his arm. Cas followed jealously with Meg clinging to his own arm. The other groomsman was a different cousin of Andrea’s that Dean and Cas didn’t know with Ruby as the third bridesmaid. She avoided both Dean and Cas’s eyes. They all got settled up front and waited. 

Finally, Andrea walked down the aisle. She walked slowly and graciously to the front of the church to face Benny whose face was pure joy. 

The rest of the service was great except that Cas was standing so close to Dean but couldn’t touch him which was torture. 

 

The subsequent reception was an all-out affair. The large group went to an upscale hotel very close to the church that had a large ballroom with a chandelier. They ate a lavish meal of parmesan chicken, garlic potatoes, different soups and vegetables. 

At the high, long table where Benny, Andrea and their groomsmen and bridesmaids sat, Dean was next to Benny and Cas. The bridesmaids were in a row on Andrea’s side. Dinner was finishing up and it was continued torture for Cas to just sit next to Dean but not hold his hand or anything. He was sitting close enough to bump his knee against him a little but that was all and Cas wanted more.

“I really want to rip that tux off you,” Cas whispered in Dean’s ear, unable to fight it anymore. Dean shifted in his seat and got a little pink in his cheeks wondering where this was coming from. 

“Whoa, Cas…” Dean said quietly as Cas moved his hand up his leg. Dean looked around to make sure no one was looking at them. He wasn’t going to question a good time. “Follow me.”

Cas matched Dean’s mischievous smile and was on his heels out of the huge room before they escaped into the coatroom. Once they were in, Dean slammed Cas against the door to shut it. 

“Been wanting this all day,” Dean murmured against Cas’s mouth before kissing him, hard. “Look so damn good in that tux,” he breathed before kissing him again. 

Dean pressed his whole body against Cas and found that he was as hard as he was. Dean moved to kissing and sucking at Cas’s neck instead, which made Cas moan and grab Dean’s shoulder’s. Dean’s hands moved to rub over Cas’s pants and he started to undo his belt. 

Dean kissed him again, lowering Cas’s pants and taking his length in his hand.

“Dean,” Cas moaned as Dean stroked up and down. 

Dean smirked as he sunk to his knees in front of Cas and replaced his hand with his mouth. Cas couldn’t make coherent words as Dean took all of him in his mouth and continued the motion he started with his hand. 

“Fuck,” Cas huffed.

Dean made obscene noises as he bobbed his head up and down, taking all of Cas in his mouth like a pro. He kept going until Cas fell over the edge. 

Dean stood up, helping to support Cas whose legs were pretty weak, and made sure his mouth and chin were clean before pulling Cas’s pants back up. 

Cas knew Dean was still hard because he loved seeing Cas spent like this after he took care of him. Once his own pants were on, he turned them around to slam Dean against the door to return the favor. 

He felt like he lacked skill in this area but the sounds Dean let out made him think again. Dean tangled his hands in Cas’s hair as he brought him to climax.

“Shit,” Dean exhaled. “You are getting good at that.”

 

After a little more time spent in the coatroom, the two made sure the coast was clear before sneaking back into the ballroom. Benny gave them a knowing glance but didn’t say anything. They took their seats again in time for the cake being served. 

“I guess we missed them cut the cake,” Cas observed. 

“Oops,” Dean shrugged.

“It was worth it,” Cas smirked. Dean leaned over enough to bump him with his shoulder. 

They finished their cake in time for a familiar song to come on.

“Hey, it’s our song,” Dean mumbled through his last mouthful of cake.

Cas listened for a moment. It was “Faithfully.”

“When did we decide we had a song?” Cas asked.

“I did when I told Benny to make sure to play it,” Dean grinned, swallowing his cake. “We… you know what?”

“What?” 

“Fuck everybody. I want to dance with my boyfriend,” Dean said firmly. He took Cas’s hand and led him to the dance floor.

“Dean, are you sure?” Cas wondered.

“Damn sure,” Dean said, grabbing one of Cas’s hands and putting his other one on Cas’s hip. Cas placed his other hand on Dean’s shoulder and nervously looked around. 

Crowley had a smug look as did the rest of the gang, like they knew all along and couldn’t wait to use it against them. Some older relatives of Benny’s and Andrea’s had looks of what might have been disgust, being from the South and all. Cas didn’t care one bit. He only cared about Dean. 

“We should have gone together in the first place,” Cas pointed out, trying to hide a smirk. 

“I know, I know. You can say ‘I told you so,’” Dean said, but with a smile. Cas was always right.

“I’d rather say something else,” Cas said. If there was ever a time…

“What?” Dean asked with confusion etched on his face. Dean felt Cas’s hands tighten.

“I love you,” Cas said before he could chicken out, looking right into Dean’s eyes. The confusion held for a second and then what was almost panic. 

“I just…” Cas started, wondering if it was a bad idea to say what he did. He was going to say “I just wanted you to know,” but was stopped.

“I love you, too,” Dean blurted. He still looked a little panicked but took a deep breath and relaxed. “Probably have since we first kissed I was just too…scared, I guess, to say it.”

“You almost did, when you were drunk once,” Cas admitted.

“So, I did say it first,” Dean said with trademark cockiness.

“Is everything always a competition with you?” Cas rolled his eyes. 

They kissed briefly before Cas continued. 

“I loved you since we watched the fireworks at Navy Pier.”

“We really should have said something earlier,” Dean shook his head and laughed before kissing Cas again. 

_I'm forever yours....Faithfully_ , the song played on as Cas pulled his boyfriend closer.

Dean and Cas continued to dance until the song finished. Cas couldn’t believe that being arrested for stealing a car that Gabriel actually stole all those months ago could have led him to Dean but he wouldn’t have changed it for the world. But now he had to do everything possible to hold onto him and protect him from Henriksen and Mills. 

Cas still held Dean close even though the next song was quicker. He knew things were going to get bad, tonight and the coming days, and he just wanted to hold Dean. They had finally said “I love you” and he wasn’t going to let go that easily. 

Some of the extended family had left so it was mostly just their gang when they were interrupted.

“What the hell are you doing here?” Crowley snapped. 

The room got quiet, people stopped talking and Cas was pretty sure the DJ turned the music down. Cas and Dean broke apart but stayed close. Dean’s hand moved to hover over his lower back where his gun always was. 

All heads snapped to the ballroom’s entrance to see who Crowley was yelling at. Cas had been focused on Dean and didn’t realize someone had shown up.

“I’m here to help,” the surprise guest replied, hands in the air. It was Lucifer. He walked to meet Crowley in the middle of the huge room, mere feet from Dean and Cas.

“You? Help? Last time, you started an all-out war!” Crowley sneered. Cas cringed at the memory of Dean bleeding in his lap. It was something he didn’t care to dwell on.

“Oh, that was just a little bit of fun for me but this is different.”

Crowley didn’t bother with a response, just waited. In the huge room, everyone seemed to collectively hold their breaths waiting for Lucifer’s answer. If Lucifer was here, it couldn’t be good. The rest of the gang had gathered around them.

“Michael and company are here,” Lucifer announced, “just outside this hotel.” 

Cas refrained from letting out a gasp. He knew they were coming but what was Lucifer doing here? And where were the cops?

“Really? And they just let you in?” Dean butted in, speaking without thinking like usual. 

“Winchester,” Lucifer rolled his eyes, “always a pain in my ass.”

“That’s me. Now, tell us how you got in and why we should trust you,” Dean demanded.

“I snuck in a side door and you should trust me because I was nice enough to share this information.”

“Out of the goodness of your… I hesitate to say heart since you don’t have one…” Crowley rambled. 

“You’re my customers, my mules. If you all die, them too, that’s bad for business,” Lucifer explained. Cas had to admit that, while twisted, was sound logic. 

Crowley glared, weighing the truth of Lucifer’s words against his own stubbornness. 

“All right, everyone out. I presume you won’t mind showing us this side door?” Crowley said, still with a slight sneer. He really didn’t want to have to listen to Lucifer. 

The few remaining family members of both Benny and Andrea were lead out first. They were just about out when the ballroom doors unexpectedly opened again. Those evacuating started to run while Crowley and his gang pulled out their guns to greet Michael and his gang. 

“What do you want, Michael?” Crowley greeted. 

“You will pay for Adam’s death. All of you!” Michael stated, unnervingly calm. 

What happened next was a blur. A confusing blur of doors opening on all sides, cops swarming in, people running in all directions… Dean grabbed his hand and pulled him, shots were fired…

The ballroom had become a battlefield and bullets were whizzing everywhere. Dean and Cas barely made it through the side door and left everyone behind. 

“We need to get to Bobby’s,” Dean said, out of breath as they ran out of the hotel and to the car.

“What about Meg and Lilith?” Cas asked. He hadn’t wanted them to be their dates but he didn’t want them to get hurt either. 

“They’ll be fine. Those guys are douchebags but they won’t hurt the girls,” Dean explained, flooring the gas. Cas hoped no one on either side got hurt this time. 

Once they reached Bobby’s garage, Dean texted the rest of the gang to show up. Within fifteen minutes, they were all there, even Benny. Well, almost all of them.

“Where’s Dick?” Crowley asked Edgar.

“We were running, cops got him,” Edgar answered. Concerned murmurs went through the group.

“All right, we need to focus. Clearly, cops are cracking down on all of us and they somehow knew Michael’s gang was going to be there,” Crowley said. 

Crowley seemed to just be thinking out loud to himself. His eyes scanned the group but seemed to linger on Cas longer than anyone else when he mentioned the cops but maybe he was just being paranoid. 

“So, what do we do?” Gordon asked. 

“We lay low, be careful. But keep selling,” Crowley decided. 

“Keep selling? Are you fucking kidding me?” Dean exploded. Dean and Crowley each took a step towards each other.

“We don’t stop because of a little…inconvenience,” Crowley drawled, glaring at Dean who glared right back. “Dick will be back soon enough.”

“This is a little more serious than that,” Dean snapped. 

Crowley clenched his fists and started to step forward again. Dean moved too but Cas grabbed his arm to stop him. The two of them fighting wouldn’t solve anything. 

“Dean, don’t.”

Immediately when Cas touched him, Dean relaxed and stepped back.

“Listen to your boyfriend,” Crowley jeered. 

Cas knew right away that was the exact wrong thing to say to Dean. 

Before Cas or Crowley could do anything to stop him, Dean’s fist flew into Crowley’s face with a satisfying crunch. Crowley took several steps back, his hands clutching his bleeding and probably broken nose. 

“Anyone else got a problem?” Dean announced. No one else did. 

Without a word, Dean stormed out of Bobby’s with Cas close behind him.

 

~~~

 

Dean and Cas got situated on their usual street corner the next day after the wedding. Cas was nervous about selling with the added pressure from the cops and Dean, while he might have been just as scared, didn’t say anything. Benny was on his brief honeymoon back home in Louisiana with Andrea. 

“Stop doing that,” Dean said, exhaling smoke from his cigarette and glancing at Cas.

“Doing what?” Cas replied defensively, although he knew what Dean meant. 

“Looking back and forth all shifty-eyed,” Dean said, motioning back and forth with the hand holding the cigarette. 

“I am not,” Cas refuted. Dean looked at him out of the corner of his eye. Cas shrugged. Maybe he had been but he didn’t want to deal with the police. 

Cas’s heart almost stopped when a car pulled over to the curb in front of them. It was only Crowley. Cas let out a sigh of relief.

“Hello, boys,” he greeted. 

“Nice shiner,” Dean smirked, inhaling off his smoke. He had a bandage over his nose and his right eye was black from the injury. Crowley didn’t comment about it.

“Just thought you should know Uriel and Zachariah were picked up by Henriksen and that lady cop,” Crowley explained.

“Good, they were dicks,” Dean said, crushing his cigarette butt on the ground. 

“Don’t get arrested,” Crowley advised before driving away. 

“He’s so helpful,” Dean rolled his eyes. 

“Dean, he’s right,” Cas pointed out, “we need to be careful.”

“All right, all right, we’re almost done,” Dean said, checking his pockets for how much more weed he had left to sell. 

“Uh, Dean…”

“What?” Dean asked, his head snapping up.

“I think we need to go now,” Cas said, pointing to the cop car that was driving up. 

“Fuck,” Dean cursed, “follow me.” 

Rather than stay around to chat with the police like he did with Benny, they took off. Dean led Cas away, hopping his regular fence using the dumpster and taking off down the alley. 

 

Once at Dean’s apartment, Cas received a text from Balthazar. 

Balthazar: **Any of your guys get picked up besides Dick?**

Cas: **No, any of your guys besides Uriel and Zachariah?**

Balthazar: **No, but they’re really cracking down. Be careful.**

It was a good update but nothing Cas didn’t already know. It was also weird that Balthazar was helping him and seemed concerned. 

Cas’s phone buzzed again.

Mills: **We have a plan. Can you come to the station?**

Cas was going to reply when Dean checked his own phone and looked at Cas.

“Crowley texted. We’re all meeting up.”

“I…uh, I can’t. My brother needs me to come home,” Cas lied. 

“Cas, this is kind of important,” Dean insisted, crossing his arms. 

“I know. I’ll catch up with you later,” Cas said and hurried out the door after a very brief kiss, leaving Dean dumbstruck. 

 

“What’s the plan?” Cas asked as he sat down with Henriksen and Mills. 

“The best way to bring both sides down is to take down Lucifer,” Mills started. Cas had to agree there, after all Lucifer supplied both sides. 

“Now we know what he looks like, so it’ll be easier,” Henriksen continued. They didn’t catch him at the wedding but they knew his face now.

“What do I have to do?” Cas said, cutting to the chase. 

“We want you to wear a wire and talk to Crowley. Figure out where we can find Lucifer and try to get dirt on both of them,” Mills explained. She glanced at Castiel, curious to his response.

“I…” Cas swallowed. This was maybe the craziest thing they had asked him to do but it had to be done. 

“We need this, before anyone else gets hurt,” Henriksen said, oddly compassionate. “We have to start at the top of the pyramid here.” 

“Fine,” Cas agreed. They gave him all of the equipment he needed and told him how to work the little microphone before he left the station. 

 

Crowley was on the phone but stopped when he saw who had just walked out of the police station. 

“I have to call you back,” Crowley said before hanging up. He watched Cas go and continued the other way towards the meeting he called with his boys, one he guessed Cas wouldn’t be at. 

At Bobby’s garage, Crowley called them all to order. 

“All right lads, let’s get to it. Another one of our own was arrested today,” he began. 

“Hope it was Castiel,” Alastair muttered. Dean moved towards him with a clenched fist ready to give him the same makeover he gave their leader.

“Dean, knock it off. Protect your boyfriend’s honor on your own time,” Crowley commanded. 

Dean reluctantly followed the order although every instinct he had said to pound Alastair into the ground. There would be time for that later, though.

“Gordon has been arrested. But to even it out, so has Raphael. I need all of you to move corners, even by a little. Sell somewhere new. No need to make this easy for ‘em,” Crowley ended. 

Everyone turned to go, including Dean but he was stopped.

“Dean, a moment?” Crowley asked, making it not much of a question. 

Dean paused, got bumped by Alastair on his way out, then made his way over to Crowley. The garage was empty except for the two of them. 

“Where was Castiel?” Crowley pried. 

“Couldn’t make it,” Dean stated simply. 

“Would it be because he was too busy with the cops?” Crowley asked. 

Dean titled his head and his face was etched with confusion as his stomach dropped. Did Cas get arrested, was he okay?

“I’m sure he’s fine,” Crowley assured, “I saw him walking out after I bet he sang like a bird.”

“He wouldn’t,” Dean defended. “Not him.”

He didn’t entertain that idea for a second because it was so crazy. There was no way.

“Don’t be so sure,” Crowley said, leaving the garage.


	11. Chapter 11

It was a dreary, cold October Monday. Castiel had the wire on from the cops and it felt obvious that he was wearing it. He looked in the floor length mirror in his room and it seemed so clear what was under his shirt. Over his t-shirt, he had a loose button-up blue shirt to try to conceal the mechanism. The tape holding it in place would surely unstick, Cas figured, since he was sweating so much.

_He’s going to know,_ Cas thought pessimistically, _Crowley’s going to kill me._

Cas set up a meeting with Crowley at the Roadhouse and Cas was glad it was somewhere public. 

Once there, he sat across from Crowley at the tiny table. It was lunchtime but not very crowded. 

“So, you missed the meeting yesterday,” Crowley stated matter-of-factly. 

“I did,” Cas replied. There was no use arguing that. 

“Where were you?” Crowley asked, taking a drink of what looked like scotch despite being the middle of the day. 

“I…uh, I had to…” Cas stammered. He hadn’t thought that through. 

“I saw you leaving the police station.”

“Right, my brother was there,” Cas lied. Crowley raised his eyebrows in disbelief. 

“So, you’re still pretending you’re not a snitch,” Crowley said. 

“I’m not a snitch,” Cas lied again. 

“I know you tell the cops our locations to sell, where we get our drugs from, everything about out little operation.”

“Look, I want to find Lucifer,” Cas interrupted. Crowley paused, his drink halfway to his lips. 

“Now, why would you want to do that?” Crowley asked, looking genuinely concerned for Cas’s mental health. Cas couldn’t blame him. 

“I want him to stop pinning the groups against each other,” Cas explained truthfully. “I want people to stop dying.”

“He wouldn’t, gets too much of a kick out of it,” Crowley laughed, sipping his scotch. “He’s my boss, I can’t sell him out. Besides, so what if Michael’s guys die?”

“I care,” Cas asked, remembering Adam who was just in high school. What about his mother? How could Crowley be such a, as Dean would put it, dick?

Crowley rolled his eyes.

“Just tell me where he is,” Cas demanded. 

Crowley did just that after a moment of consideration.

“And you say I’m a rat,” Cas taunted. 

“I’m only telling you because I hope Lucifer guts you like a fish,” Crowley glared. “Your boyfriend may trust you but I don’t.” 

 

Castiel immediately took the wire back to Henriksen and Mills.

“Any trouble?” Mills asked. Cas shook his head.

He waited while the two officers listened to the tape.

“Well, now we know where Lucifer is and there should be enough probable cause, with our other evidence, to get an arrest warrant for Crowley,” Henriksen said. Cas let out a sigh of relief. 

“Good work,” Mills said. 

Cas exited the station and he felt like a weight was lifted off of his shoulders. Maybe, just maybe, arresting the two of them would be enough and the gang would fall apart and Dean could walk free. They could be happy once Cas wasn’t constantly worried that Dean was going to find out what he had been up to the whole time he had known him.

 

Right after Cas left the station, he called Dean.

“Please don’t tell me you’re pregnant,” Dean answered.

“That isn’t biologically possible, Dean. Why…”

“Sorry, I was on the phone with Lisa,” Dean sighed. “She’s having a crisis on whether or not she wants to keep the baby.”

“Oh,” Cas said in a small voice, not really sure what to say.

“Do you want to come over?” Dean sighed again. “I could use a distraction.”

Cas said he could too and began to walk towards the apartment.

Sam was at the table doing homework when Cas showed up. He sat on the couch next to Dean who suggested they watch a scary movie because it was October after all. 

“How about _Friday the 13th_?” Cas suggested, seeing it on the shelf next to the TV.

“The original or the remake?” Dean asked. “Classics are always better.”

Cas got up to get the DVD off the shelf to look closer. “The remake.”

“Why do we own that one?” Dean asked, looking accusatorily at Sam. 

“I like the remake better!” Sam protested. 

Dean rolled his eyes. They put it on but Sam didn’t stay long. He went to hang out with Jessica, though she was still pissed, because she was willing to give him a second chance. Sam was determined to make it right.

Crowley’s words echoed in Dean’s head about Castiel being a narc but he shook them off. It simply wasn’t possible for the bookworm to be the cops’ tool.

Dean and Cas sat on the couch, snuggled up, watching the movie. It wasn’t very good but neither of them really cared. 

It was great because both of the boys’ minds weren’t on their current issues until Dean’s phone rang. 

“Hello?” he answered. He untangled himself from Cas and went into his room, shutting the door part way but enough that Cas couldn’t hear what was going on. Cas paused the movie then his own phone buzzed in his pocket. 

Balthazar: **Cops got Lucifer and Crowley.**

Cas didn’t think that the cops would be so quick and efficient. He prayed, which he hadn’t done since Dean had been shot, that the phone call in the other room didn’t have anything to do with those two being arrested. A sinking feeling in his gut told him otherwise. 

“Cas,” Dean said, walking out of his room with his phone held tightly in his hand, “is there something you want to tell me?”

“I…” Cas swallowed hard, scared where this was going. He stood up off the couch.

“That was Crowley. I was his phone call and he wanted to let me know he got arrested. Do you know anything about that?” Dean looked hard at Cas. 

There was no way Crowley was right, no way, but Cas looked like a scared animal backed into a corner. Every instinct told him Crowley was telling the truth but he needed to try to remain loyal.

“Dean, let me explain,” Cas caved.

“Son of a bitch.”

“I can explain!” Cas insisted.

“Explain how you lied to me? How you were working for the cops, the fucking cops, the entire time?” Dean yelled the last three words. 

Cas’s mouth was dry and he couldn’t speak. This wasn’t supposed to happen, he was supposed to save him.

Dean stepped closer. It was too real.

“I defended you, countless times, to those assholes. And they were right,” Dean shook his head and let out a bitter laugh.

“I didn’t have a choice. The cops were going to arrest me and my brother, it was the only way,” Cas tried a last ditch effort to explain himself but the words sounded stupid coming out. 

“I could have helped you, why didn’t you just tell me?” Dean said quietly. 

He seemed so broken at Cas’s betrayal he almost just didn’t answer. He didn’t want to hurt him anymore.

“Would you believe me if I said I was trying to protect you?” Cas tried in a small voice. 

“Did you…” Dean started but stopped. “Cas, was any of it true?”

Cas didn’t know what he meant and kept quiet.

“Do you even care about me or was that a lie, too?” Dean said, words dripping acid and burning Cas to the core. 

_After all we’ve been through, how could he say that?_ Cas thought before he answered. 

“Falling in love with you wasn’t supposed to happen.”

Dean laughed bitterly again.

“Yeah, well, I hope you’re glad you made me fall in love with you,” Dean said, his voice getting softer as he looked at the ground. “How could you do this, Cas?” His voice had gotten so diminished Cas almost didn’t hear him but the heartbreak was clear.

“Dean, I’m sorry. I thought I was doing the right thing,” Cas admitted. 

He had tried, so hard, to keep Dean from getting hurt, but now he was the one hurting him. Even saying he loved him now felt different, wrong, since he had sold him out.

“Well, you were wrong,” Dean spat, looking back up and right at Cas.

“Dean…” Cas attempted. He had to make him understand. 

“I think you should leave.”

“Dean…” Cas begged, reaching out to grab Dean’s shoulder but he jerked away.

“Go,” Dean said, now facing away from Cas.

Cas left, letting the tears he had been holding in flow down his face once he was in the hallway. Dean sat on the couch, dropping his head into his hands.

 

Even though it went against his better judgment, Dean took control of the remaining group members. Without Crowley, he was in charge and would try his best to keep them out of the hands of the cops even if they were grade A douches besides Benny. 

Dean texted Alastair, Azazel, Jake, and Edgar, since they were the only members who hadn’t been arrested, as well as Benny who was back from his honeymoon. 

The small group gathered in front of their normal store. Dean sighed as the guys walked up. He couldn’t help but think of when they would gather, all of them, with the cops being only a distant threat. Now, it was like they kicked it into high gear and weren’t going to stop until everyone was in jail. Dean figured it was since they had some extra help. Cas…

_No_ , Dean chided himself, looking up and blinking away the hot tears forming, _you did enough crying, don’t you think?_

So, his boyfriend sold him out and probably never loved him. Dean wasn’t going to sit around with a tub of Hagen Daaz and sob into it. He and Cas hadn’t talked since their fight three days ago but that wasn’t the problem right now. Dean had to focus and he was going to be smart and stay out of jail. He snapped out of it as the gang assembled. 

“Where is everyone?” Benny asked, showing up and shaking Dean’s hand. 

“Ask this dumbass,” Alastair sneered, gesturing to Dean.

“Everyone who isn’t here got arrested,” Dean explained to Benny. There wasn’t any use in avoiding the topic. Clearly, the guys knew what had been going on and why. 

“Cas too?” Benny asked. Dean’s stomach dropped and he froze up, not sure what to say. Saying it out loud, that Cas had betrayed them all, was too much for Dean to handle.

“Yeah, Dean, where’s your boy toy?” Jake asked, obviously well aware of the situation. “Explain that to us.”

“Some leader…” Edgar scoffed.

“Crowley was right,” Dean admitted reluctantly as he cut Edgar off, “Cas was a snitch.” Both of those phrases made him sick to his stomach.

“Seriously?” Benny asked in disbelief. Dean looked down which gave Benny his answer. 

“It doesn’t matter,” Dean said to the ground, trying to believe the lie.

Before anyone else could say anything, the whir of cop sirens rang out and the group instinctively ran in all different directions. 

Someone yelled, “Run!” but didn’t need to. It was habit to book it in the opposite direction of those red and blue lights. 

Benny and Dean headed down the same street. Dean counted about three cop cars before they were out of sight.

“Got Alastair and Azazel,” Benny huffed as they ran. Dean didn’t bother turning around to see them get arrested. The boys turned a corner. It seemed like they were in the clear but kept running just to be safe. 

“And then there were four,” Dean joked humorlessly as they ran. Used to be, running from the cops was a great adrenaline rush and Dean loved it. Now, he was just tired.

The two got to Benny’s restaurant before going separate ways.

“Just stay with Andrea and lay low, you hear?” Dean said. Benny nodded.

“Stay safe, brother,” Benny said, pulling Dean in for a hug. “I’m sorry about…”

“Thanks,” Dean cut him off and broke the embrace. There wasn’t any point in talking about what Cas had done. It was over. Benny nodded again in understanding and they split up.

 

~~~

 

Dean drank whiskey, alone, in his apartment. It had been a shitty week that went south so fast, faster than Dean could have ever guessed. In less than a week, his boyfriend told him he loved him and then had screwed him over. Hell, Dean had said he loved Cas right back. This was probably why he never said it to anybody. Ever. Of course this was the result. He was left, alone, with just whiskey for company. And not even good whiskey. 

He finished his glass and got off the couch to get more. In the kitchen area, he poured the rest of the bottle into his glass. Looking into the brown liquid, he tried to regret loving Cas but he couldn’t. He took a large drink, letting the burn of the alcohol begin to wash away the pain and make him numb. Nobody made him feel the way Cas did even if Dean never meant anything to him. 

That thought pissed him off and he finished drinking before whipping the glass at the wall. He sank onto the couch and just stared hopelessly at the broken glass on the floor and the new, small dent on the wall.

His phone rang on the couch next to him, interrupting his alcoholic pity party.

**Incoming Call: Cas.**

“You’ve gotta be fucking kidding me,” Dean said out loud and with a slight slur to the empty apartment. Dean really wasn’t in the mood but he had drank enough that he answered.

“What?” Dean snapped. Cas really had a lot of nerve…

“Is this…uh, Dean?” a nervous sounding woman asked on the other line. 

“Yeah, who’s this?” Dean asked, very confused and trying to sound nicer.

“I’m calling from the hospital. We have a patient here, this is his phone, and he keeps saying ‘Dean.’ Do you know…”

“I’m on my way,” Dean said, hanging up. No matter what Cas did, Dean would rush to his side without hesitation. He threw on his leather jacket and boots then grabbed his keys. 

Once he left the apartment building, he blinked a couple times. He came to the realization that it would be best if he didn’t drive right now. He wasn’t sacrificing himself or his baby for anything. There was no way he would put himself in a position to leave Sam alone with just a shitty apartment and a totaled car.

Dean stood on the street, hailed a cab and headed to the hospital and to Cas.

It was pretty damn sobering to ride in a taxi and worry about someone you cared about who was in the hospital. Dean had panicked and didn’t even bother to ask what had happened. Guilt trickled its way into his brain. They hadn’t talked since their fight. He could lose Cas and the last thing he told him was to leave, to get out. Maybe Cas never loved him but Dean sure as hell loved Cas and even if he was pissed, that didn’t change. 

Once Dean finally got to the hospital after what felt like the longest car ride in history, he threw some money at the cab driver, grossly overtipping in his haste, and rushed inside. He quickly got instructions to Cas’s room, ignoring the nurses who complained he wasn’t family and visiting hours were just about over. 

At the doorway to Cas’s room, Dean paused. The door was shut and he had his hand on the doorknob, hesitating to go in. Cas might not want him here. Dean took a deep breath and opened the door. He had to know if Cas was okay.

Dean took one step into the small room before someone slammed into him and knocked him down. The two struggled and grappled on the floor. The man, shorter than Dean by several inches, landed a good punch to Dean’s cheek. Dean finally formed a coherent thought and pushed his assailant off. They stood facing each other, breathing heavy.

“Here to finish the job?” the attacker asked. 

Dean had no idea what the guy meant or why he thought he would want to hurt Cas, but took a quick sideways glance at the occupied bed in the room. Castiel was in it and he didn’t look good. His face had scrapes, cuts and bruises and his right arm was heavily bandaged. And that was only what Dean could see above the blanket covering him. 

“I could ask you the same thing. You’re one of Michael’s guys,” Dean retorted with a glare, recognizing the guy. 

“And you’re one of Crowley’s,” the other guy pointed out, also with a glare. Neither man moved.

Dean wasn’t sure how much this guy knew. If he thought Dean was pissed, like everyone else in their gang, that Cas sold them out, it would make sense he would be here to finish him off. Revenge was kind of a big aspect in this life. But so were pride and rivalry.

“I get it, he’s in the rival gang and you’re here to hurt him…” 

“What? No, seriously? This guy?” the man laughed for a reason unknown to Dean. “In a gang?”

Dean, again, was confused. “Then why are you here?” 

“He’s my brother.”

“What?” Dean asked. 

Dean thought back and realized that Cas had described the relationship he had with his brother as turbulent but never said the guy’s name.

“Yeah, I’m his brother. Why the hell are you here?”

“I’m his…” Dean stumbled on the word boyfriend. It didn’t seem accurate anymore. “I’m Dean.”

“Oh, no way,” the guy laughed again. “Of course, you’re Dean. Heard a bit about you.” 

Dean didn’t know what to say. Cas’s brother’s face fell as he seemed to realize something. 

“Oh, shit. You’re…you’re his Dean? But you’re with Crowley’s gang!” he repeated. 

“I know.”

The big brother stepped into Dean’s space and grabbed his shirt, shaking him. 

“WHAT DID YOU DO TO HIM?” he yelled. The sound must have woke Cas up because he coughed, making the two step back and stop fighting. Dean understood the protective older brother role, but Dean didn’t have anything to do with why Cas was hurt. 

“Cas, hey,” his brother went to the side of his bed, suddenly calm. Dean stood awkwardly at the end of the bed, not sure what to do or say. He was glad Cas was reasonably okay but that didn’t change what had happened between them. 

“Dean,” Cas gasped, turning from his brother to look at him. Dean now walked to the other side of the bed as his brother got some water for Cas. 

“What the hell happened to you?” Dean asked, hands in his pockets. He honestly didn’t know what else to say.

“Jake and Edgar,” Cas said, throat dry. He sat up enough to drink the water given to him.

“Told you it was your people’s fault,” the brother muttered.

“Listen, douchebag…”

“Gabriel,” he snapped. 

“Whatever.”

“Do you guys know each other?” Cas asked, his eyes going back and forth between the argument hovering over his bed. 

“He’s in Michael’s gang. He helped beat me up that day we had our date to Navy Pier.”

“I… what? No way,” Cas asked, looking at Gabriel with disbelief. 

“And why do you know Dean?” Gabriel changed the topic, gesturing at Dean and practically spitting Dean’s name like it was a foul word.

“He… uh, he’s…” Cas said, also struggling with what to call what their relationship had dissolved into. He was also kind of hung up on the fact that his brother was in a gang. It would explain why Lucifer said Cas should be in the other gang. 

“He’s in Crowley’s gang,” Gabriel argued.

“I know, that’s kind of how we met.”

“You joined a gang?” Gabriel asked, now the one to look shocked. “Did he get you to join?”

“Well…”

“Technically, he was just snitching on us all if that makes you feel better,” Dean muttered, crossing his arms over his chest. Reopening that wound hurt and he wished they hadn’t. 

“Dean, please, you have to…” Cas begged.

“I don’t have to do shit,” Dean snapped.

“Okay, I’m going to give you some space here,” Gabriel said, taking a couple steps towards the door. “I trust you’re not going to hurt my baby brother?”

Gabriel took Dean’s glare as his answer and backed out the door. 

“Dean…” Cas started again.

“Cas, look, I just had to make sure you were okay. You’re banged up but reasonably unhurt so I’m going to go. I need to avoid getting arrested, remember?”

The hurt on Cas’s face was enough to make Dean look away. He turned to walk out the door and almost ran into Cas’s two new visitors. 

It was Henriksen and Mills. 

There was a brief moment of hesitation where everyone froze. If they had been arresting everyone in both gangs, there was nothing stopping them from arresting Dean. It was a sickening thought to know Cas have ratted on him, too. Dean had a slight deer-in-headlights moment before regaining his confidence. 

“Evening, officers,” Dean joked. “Here to actually do some good?”

“Winchester, I should arrest you right now,” Henriksen said, stepping towards Dean.

“Do it,” Dean said, straightening his arms in a “come at me” pose. “Show me your warrant. Or tell me the crime I’m committing right now that gives you probable cause to arrest me.”

Henriksen tightened his lips in a line and glared at Dean.

“Didn’t think so,” Dean said as he sidestepped the two. “Just catch the assholes that did this to Cas.”

“Oh, we will,” Henriksen said to Dean’s retreating back, “then we’re coming for you!”

“Bring it on!” Dean yelled as he walked down the hallway. He kept up the bravado but knew he was royally fucked.


	12. Chapter 12

Cas watched Dean go and winced when he yelled at the cops to bring it on. Castiel didn’t want the cops to bring it on, he wanted for Dean to be left alone. If only things could go back to how they were before Cas told the truth. 

“So, you know your attackers?” Mills asked, sitting on his right. Henriksen remained standing with his arms crossed. 

“Yes. Jake and Edgar,” Cas responded before drinking more water with his uninjured hand. His split lip hurt when the cup touched his lips. 

“Why did they attack you?” Henriksen wanted to know. 

Cas gave him a glare. 

“Right, the snitching,” Henriksen figured. “I’m guessing that’s why your boyfriend was all huffy?”

“Henriksen,” Cas sighed, closing his eyes briefly before opening them to continue. “I am really not in the mood. If you would please just go, I would appreciate it.” It took all of Cas’s willpower to gently but firmly say what he wanted to scream instead. 

“Fine,” Henriksen snapped. “Just know I wasn’t kidding when I said we were going after Dean next. You were nice enough to give us all of the information we needed.”

Cas closed his eyes and kept them shut as he listened to their retreating footsteps. Henriksen really didn’t need to remind him how he ruined Dean’s life. Cas was all too aware and hated himself for it. Hell, he thought he got off easy by being beaten up. He knew he deserved a lot worse. A single tear rolled down his cheek and he didn’t bother to wipe it away. 

Gabriel returned. Cas didn’t notice he was back until he cleared his throat on his left. Cas opened his eyes as Gabriel sat. 

“Saw Tweedle-Dee and Tweedle-Dum leave your room,” Gabriel observed. “I know my guys have had problems with them in the past. I’m guessing your guys have, too.”

“They aren’t ‘my’ guys, Gabriel,” Cas said, making air-quotes. “Did you miss the part where I was an informant?”

“I still find it hard to believe.”

“What? That I was in a gang?” Cas questioned. 

“Yeah,” Gabriel shrugged.

“Well, I find it hard to believe you’re in one, too. We’ve run into you guys countless times. How have I not seen you?”

Gabriel just wiggled his eyebrows.

“Seriously,” Cas rolled his eyes. 

“I have my ways. I’m pretty much off the cops’ radar even.”

“You know, I joined to keep you safe,” Cas admitted after a pause. Gabriel looked confused. “The night you boosted the car? This was why nothing happened to either of us.”

“Holy shit. Why didn’t you tell me?”

“Why didn’t you tell me you were in a gang? Same reason. To protect me.”

“We have got to work on better communication little bro,” Gabriel smiled. Cas agreed. 

 

Dean walked home from the hospital which took longer than he would have liked. Time was of the essence here because he was basically on the run. That idea sounded cool to him when he was a kid but it certainly held no appeal at the current moment. 

He hurried to his room and threw some clothes into a duffel bag. Before he left the apartment, he scribbled a quick note for Sam. It simply told him to go to Bobby’s, no other explanation. But Sam wouldn’t need one, he would listen. He left the keys to the Impala on top of the note. 

With his hand on the doorknob to the apartment, he paused and looked back. After so many shitty memories here mixed in with some good ones, it felt weird to leave. He didn’t know if he was coming back anytime soon. He shook off the pointless nostalgia and shut the door.

Before checking into a motel room several miles from the apartment for the night, Dean stopped at a liquor store. It was very late now and several less than friendly characters were lurking around inside the store and out. He purchased his whiskey with his fake I.D, a more expensive brand than usual because why the hell not at this point, and walked out. 

Besides getting interested glances from obvious prostitutes and glares from scary looking tough guys, Dean made it to the motel without a problem. It was seedy but nothing he couldn’t handle. He kicked off his boots and sat back against the headboard of the bed with his booze. 

As he drank, he couldn’t help but picture Cas in that hospital bed. He had seemed so… Dean hated to use the word weak to describe Cas, but it fit. Dean knew he was anything but that and he didn’t like seeing Cas look like that. Cas had seemed small and upset. If Dean didn’t trust Henriksen and Mills to get the job done, he’d go after Jake and Edgar himself.

Dean sipped, reveling in the burn as it went down his throat. He also couldn’t go after them because now Henriksen and Mills were after him. It was still hard to believe he was on the run because the man he loved betrayed him. 

He knew what John would say. He’d tell him to man up. Get over it. That would, of course, only be the case if it were a girl Dean had been having the problems with. He’d be lucky to be alive if it were a guy while John was around. There’s a reason he only fooled around with guys after his dad died.

Dean chased the foul-tasting memory of his father away with the whiskey. The bottle was already half-empty and Dean was definitely past buzzed. It still didn’t shut his brain up so he kept drinking. 

Sam tried to call once but then Dean turned off his phone. The kid would be dragged out of the dark into his big brother’s mess soon enough, he could have one night of peace.

The bottle, now three-fourths gone, fell from Dean’s hand as he passed out.

 

~~~

 

A knock on the door woke Dean up.

“Chicago police! Open up,” came the yell from outside. 

_Fuck it_ , Dean thought, _let them come._

Dean just laid there as the door was kicked in. A group of three officers stormed in.

“Dean Winchester, you are under arrest,” Henriksen said, stepping into the room behind them. “Man, it is good to finally say that.”

“Glad you get your jollies from somewhere, Vicky,” Dean taunted as he sat up.

“Seriously? We know you’re only twenty,” Henriksen said with contempt, glancing at the bottle on the floor. 

Dean still made no effort to get out of the bed.

“Whatever. How’d you find me?” Dean wondered.

“Got a witness from your apartment to point us in the right direction and then checked motels until we found this one. Good try paying cash but this trumps it,” Henriksen said, holding up his badge. “Get up.”

Dean moved slowly to sit on the edge of the bed. Henriksen was decent enough to let him put his shoes on before pulling him up and handcuffing him.

He went with the officers without a fight. 

Dean was taken to the police station by Officer Henriksen after a silent ride in the foul-smelling car’s backseat. He remained in handcuffs and was taken into an interrogation room. Henriksen wore a smug smile the entire time. 

Mills joined them in the room right away.

“Did you catch Jake and Edgar?” Dean asked when she walked in. 

He looked like complete crap and Mills took notice. She cast a sideways glance at Henriksen who shook his head with a slight eye roll.

“Yes, we did,” she said as she sat down next to Henriksen. 

Dean nodded. At least one good thing happened as of late. They didn’t deserve to go free after what they did to Cas. No matter what the case was between then two of them, Dean never wanted Cas hurt. 

“We got guys searching through your apartment right now. Do you want to just tell us what’s there or do we have to wait until they let us know?” Henriksen asked. 

Dean didn’t say anything. He always sold all of the weed he had so it would be clean. There wouldn’t be anything there, even his gun was somewhere else. On his way to the motel he made sure to hide it at Bobby’s garage. The Impala was clean, too. He wasn’t going to let Sam drive around with something illegal.

“Fine, we’ll know soon enough,” Henriksen sighed. “I don’t think we need to spell out how much trouble you’re in, do we?”

“No, I think I got it,” Dean sat back in his chair, leaving his hands in his lap. “You can finally get a good night’s sleep because you caught me. Maybe get a wife if you can find anyone that stupid.”

Dean figured it might be the last opportunity to mess with Henriksen and he wouldn’t pass that up, however dumb it might be to poke fun at the cop that decided his immediate future. 

“We might be able to help you out,” Mills said before Henriksen had a chance to retort. 

Dean raised his eyebrows waiting for her to continue.

“Tell us everything about Crowley and Lucifer, and the others, and we can cut a deal. Maybe get you less time in jail,” Mills explained. 

“Believe it or not, there are people more important than you, smartass,” Henriksen added. “And the deal includes telling us where Benny is. He’s the only one missing from your little gang,”

“I can help with the first part but I’m not helping you hunt down Benny,” Dean stated firmly. 

He didn’t care about Lucifer or Crowley but his best friend just got married. There was no way Benny was going to jail if Dean had anything to say about it. 

“Dean…” Mills started. She was interrupted by a knock at the door. She got up to answer it. A cop was standing next to a man in a cheap looking suit. 

“Dean Winchester’s lawyer,” the cop explained before disappearing. 

“Chuck Shurley,” the lawyer said, stepping in the room. “And you two are supposed to leave now.”

“Oh, are we?” Henriksen said, standing up. He was glaring at the shorter man and even Dean had to admit that he looked a little intimidating. 

“Um…yes?” Chuck said, his attempt at bravado already fading as his voice shook.

“Fine, we’re going,” Mills said, gesturing for Henriksen to follow. The two left the room and Chuck let out a huge sigh of relief when the door shut. 

“So, you’re my PD?” Dean asked with slight amusement as Chuck sat down across from him, taking in the disgruntled man with the beard.

“Yes, nice to meet you,” Chuck answered. 

“Well, guess I’m going to jail then,” Dean smirked. 

“Hey, that… that’s not fair. I know what I’m doing,” Chuck said defensively. “But…” 

“But what?” Dean asked as Chuck took out a bunch of papers from his briefcase he set on the table. 

“They have a lot against you. Testimony from an informant is really strong evidence…”

“Can we not talk about that?” Dean groaned. 

It wasn’t just last night’s whiskey that made him almost puke. 

“Fine,” Chuck conceded. “You’re going to spend the night here then they’ll probably move you tomorrow to somewhere where you’ll be until the preliminary hearing.”

“That’s great. I just want to sleep,” Dean said. Anything besides sleep could wait. 

Chuck left and Henriksen came back in the room. Henriksen led Dean into the same cell Cas spent the night in months ago. Dean turned to face the wall and immediately fell asleep.

 

~~~

 

Castiel woke up screaming in his apartment from a nightmare. It was the first one he had had since he and Dean had slept together for the first time. 

Gabriel hurried into his room and held him until he stopped screaming and the quiet tears shaking his entire body stopped.

Cas dreamt that he was hiding from his overbearing and controlling foster mom, Naomi, in a closet. She regularly would have episodes where she would scream and throw things if chores didn’t get done or something else was wrong.

It was a memory until she started saying if Cas didn’t come out, she would hurt Dean. Cas didn’t believe her because she didn’t know Dean so he stayed. Dean should be safe. He left the closet when he heard Dean’s pained yells and then saw Naomi standing over his bloodied body with his blood on her fists. That was when he woke up. 

“Hey, you’re okay,” Gabriel said like he had done countless times before. Cas was afraid that this would happen.

He betrayed Dean and didn’t have him to sleep next to anymore. He didn’t have him as a friend or someone to talk to. Once he started falling for Dean, the nightmares had stopped. 

Now that Dean hated him, the nightmares were back but being awake hurt more. 

 

Dean was woken up late Friday afternoon by Henriksen opening his cell door. The asshole was definitely being louder than he needed to be. Dean groaned as he sat up. His mouth was dry and he had a slight headache from drinking last night. He was almost glad the cops stopped him when they did. Almost. Also, he was pretty hungry. He was having a hard time remembering what the last thing he ate was. 

Henriksen dragged him to his feet and brought him back to the same interrogation room he was in last night. Mills and Chuck were already waiting along with, thankfully, a glass of water.

Without saying anything, Dean sat down next to Chuck and downed the cup. He wondered if Sam went to Bobby’s like he told him to. They were probably both worried and confused. Dean was willing to bet the Impala that he had plenty of missed calls and texts on his phone that was taken from him when he got here. It wasn’t like him to up and disappear. He had always been there for Sam. But this time, circumstances had been different…

“Dean, did you hear what we said?” Mills asked, cutting off Dean’s train of thought. 

“No,” Dean admitted with a noncommittal shrug. 

“We wanted to talk to you about Crowley and Lucifer,” Henriksen asked.

“Okay,” Dean said. He had no problem throwing either of those dicks under the bus. 

“Crowley was the one in charge, correct?” he continued.

“Yes, he gave us the weed and told us our corners. Got the biggest cut of the profits,” Dean confessed. He knew they needed this recorded but it was annoying when he knew they already knew this.

“What about Lucifer?” Mills asked.

“He got the weed to Crowley for us to sell, that’s pretty much all I know. Oh, and he gave to Michael’s gang, too,” Dean explained, staying patient in hopes this would pay off. 

“Where did you guys usually hang out?” Henriksen pushed.

“Whoa, that wasn’t part of the deal,” Dean argued. 

He couldn’t mention Bobby’s garage or Ellen’s bar. There was no way the two of them, who had done everything for him and his brother, were getting dragged under. They didn’t really do anything anyways. Well, Ellen let them drink there and they weren’t all twenty-one but they hopefully couldn’t prove that.

Mills went to say something but Chuck, surprisingly, stepped up.

“Do you have what you need about Crowley and Lucifer?”

Mills set her mouth in a hard line and nodded.

“With this and the informant’s information we should be able to get both of them,” Henriksen said. 

Dean’s whole body tensed at the word “informant.” He didn’t want a reminder of how he got in here. To be fair, selling weed technically got him in here and he knew that but he was fine until Cas showed up in his life and changed everything. Another technicality was that he just ratted too. It was a little different because he wouldn’t lie about it to their faces. And he wasn’t in love with either of the people he just ratted on.

“Good, then we’re done,” Chuck finished.

“What now?” Dean asked, glad to think about something else. 

“You head to the Cook County Department of Corrections until your arraignment where the judge will set bail. If you can’t make bail, you stay there until the pre-trial as well,” Mills explained. 

Before leaving the station, Dean asked Chuck to give his phone and wallet to his brother to hold onto and to explain what was happening. 

 

Dean joined Jake and Edgar in the back of a Chicago Police van to be escorted to the CCDOC building. Dean specifically ignored the two of them and avoided eye contact. If they had been mad enough to hurt Cas, they would want to hurt him, too. It was Dean who brought Cas into their group and if they couldn’t get to him they would get to Dean. He could hear their whispers but didn’t care. All he did was lean his head back against the side of the van and spaced out. 

Once they arrived, it was a whirlwind of activity. Dean was sent room to room, fingerprinted and photographed then strip searched and given an orange jumpsuit with CCDOC on the back in big black letters. He moved wordlessly and did what he was told. Now was most likely not the time for his classic smartass comments. 

He was handed some bedding and other items and walked in a line with the other guys who had arrived at about the same time down a hallway. They gradually split off into their rooms they were assigned to.

The rooms each held four people. Luckily, Edgar and Jake split off before Dean. He was glad he wouldn’t have to deal with them, at least not yet. There was no guarantee he wouldn’t see them again. 

Not so luckily, he walked into a room where he came face to face with Crowley. Dean didn’t know the other two guys in the room. Dean inwardly rolled his eyes at his terrible luck.

“About time you got here,” Crowley sneered with his arms crossed and blocking Dean’s path to the one empty bed. “We got a nice little reunion started. Heard you came with Jake and Edgar?”

“Crowley, move,” Dean sighed. He couldn’t handle Crowley’s shit right now. He wanted to sleep. Last night’s bed was horribly uncomfortable and left Dean stiff. Although, this bed would probably be worse.

“Did your boyfriend come in with you?” Crowley asked, not moving. 

Dean glared. That was the one topic to stay away from, the one that would make Dean mad. Then again, that was probably Crowley’s point. 

“No,” Dean snapped, shoving past Crowley.

One hard shove from Crowley and Dean was on the floor, scraping his elbow. Dean hopped up fast and was all set to slam his fist in Crowley’s stupid, smug face before an officer stepped in from the hallway and stepped in between them.

“Play nice you two,” the big guy instructed simply before leaving again. It seemed weird to Dean that they would still be left anywhere near each other but he didn’t think too hard on it. He was too tired. 

“Just leave me the fuck alone, Crowley,” Dean demanded before picking his stuff up off the floor and throwing it on his bed before collapsing on it. 

 

Dean stayed in the Cook County Department of Corrections building that entire weekend. A handful of guys in there blamed Cas for being arrested. This meant that they blamed Dean by extension for Cas snitching so it wasn’t a pleasant weekend. They took their anger out on him frequently. There were plenty of fights and not all of them got broken up as quickly as the first altercation with Crowley. 

First thing Monday morning, he was taken to court for his arraignment. Not many injuries from the fights were visible besides a black eye. He joked with the guard escorting him that he wished he had a proper suit instead of a prison jumpsuit and that orange wasn’t his color. 

That only got him a slap on the back of the head.

Inside the courtroom, Dean was brought in to sit next to Chuck. Before sitting down, Dean turned to face the handful of people in the seats behind him. Bobby and Sam were there and they were both in suits. 

“Lookin’ good, fellas,” Dean winked. Sam’s look of disbelief and shock at his cavalier attitude combined with Bobby’s eye roll made him laugh.

That laugh died in his throat and his smile faded as his eyes landed on Castiel who was behind them. At Dean’s reaction, Cas looked down. Dean turned around and faced forward again. 

Dean honestly didn’t think Cas would show up. He wasn’t really ready to see him. The fact that Cas was in a row behind Sam and Bobby led Dean to believe that Chuck had explained the full story and Cas’s role in Dean’s arrest. Sam and Bobby couldn’t have been too happy with Castiel either. 

“The honorable Judge Missouri Moseley,” someone announced.

A short, rotund black woman came into the courtroom and the room got quiet. She had a demanding presence about her. 

“Now, Mr. Winchester…” she started when she got behind her stand. 

“Please,” Dean interrupted, “call me Dean.”

Judge Moseley’s glare effectively wiped the smirk off of Dean’s face. This woman was clearly not someone to mess with. 

“Moving on,” she said in her no-nonsense voice. “You are being charged with the felony possession, possession with intent to sell, and distribution of a schedule one substance which carries a sentence of up to five years in prison. You have the right to an attorney through all proceedings. From the evidence presented, I am setting your bail at $50,000.”

“Shit,” Dean said under his breath. There was absolutely no way that he could make that bail. 

“Do you understand what I have told you, Mr. Winchester?” 

Dean nodded.

“I need verbal confirmation,” Judge Moseley said, sounding slightly annoyed. 

“Yes, ma’am, I understand,” Dean said. 

“Will the defendant be able to afford bail?”

“No, ma’am,” Chuck answered.

“Court is adjourned,” Moseley said with a bang of her gavel. 

 

Dean spent the following week in the CCDOC trying to keep his head down. The odds were always against him in a fight and he was their favorite punching bag. Besides members of his own gang turning against him, Michael’s guys were in with them, too. The battle continued to rage between the two groups even in jail. Dean tried to stay out of trouble but it didn’t work. He never wanted to join a gang and this was why. It was petty and stupid and they were all in jail, equal levels of completely fucked. 

The following Monday was the pre-trial and Chuck had given him some legal advice. He advised him to simply plead guilty. That would avoid a lengthy and expensive trial that he would most likely lose. Also, combined with the information he provided against Crowley and Lucifer, he could probably get a reduced sentence by pleading out. 

So that’s what he did.

Right when he walked in, he looked at Sam and told him he was sorry. Sam nodded. Sam had pieced together why Dean had been doing what he was doing with the gang, with a little help from Bobby, and he understood. He was protecting him like he always had. 

Dean was too embarrassed to look at Bobby because he hated to disappoint the closest thing he had to a father and he was still mad at Cas so he turned around to face Judge Moseley. 

It was over quick. She explained that because he was entering a guilty plea and had cooperated with police by providing information, he would receive a reduced sentence. 

“I sentence you to two years with the possibility of early release on good behavior,” Moseley decided, “if you can manage that.” 

She slammed the gavel down and closed the case. 

Dean stood up and was getting ready to be led out when he felt a hand on his shoulder. Cas had run up and was trying to talk to him before they took him away.

“Dean,” Cas said, his voice pleading for Dean to listen and to understand. A bailiff had hurried off and was attempting to pull Cas off of him.

“Hold on,” Dean said to the bailiff. 

He took in the bailiff’s hard look.

“Please?”

The bailiff stepped back. 

“What do you want, Cas?” Dean asked.

“I never meant for this to happen. Please, you have to believe me,” Cas explained. “Dean, I’m sorry.”

Dean looked up to meet Cas’s eyes. He laughed, a scornful bark that sounded to Cas like Dean didn’t believe him. 

“See you in a couple years, Cas,” Dean joked before being taken away. The finality of the statement left Cas standing in the courtroom feeling hopeless. 

 

Dean had to spend one more night in the CCDOC and was grabbed from behind while he walked down a hallway. Slammed against the wall, he felt hands on his throat. His vision came back into focus and saw the hands belonged to Crowley.

“Think you can sell me out, you little maggot?” Crowley sneered right in his face. Dean struggled to form words. “Do you know how much more time I’m facing because of you?” 

Dean didn’t know and he wouldn’t have been able to tell him if he did know. His air supply was being severely diminished by Crowley’s hands. Clearly, Crowley found out that Dean had ratted on him and was pissed. This meant Lucifer probably knew, too. The sooner he got out of here, the better. Turning them both in wasn’t looking good in terms of his life span.

“Hey, hey!” a shout came. A guard ran down the hallway and pulled Crowley off of Dean. 

“Next time, you won’t be so lucky! I’ll kill you! I swear I will!” Crowley yelled as he was dragged away.

Dean caught his breath before walking the opposite directions. Two more years was going to be hell. 

 

The day after Dean was sentenced to jail, Castiel was woken up by his obnoxious alarm. He had gotten only about two solid hours of sleep and felt like shit. It had been impossible to get Dean’s cold laugh from in court out of his head and how he had looked so broken and defeated. Cas also couldn’t shake the voice in his head reminding him that it was his fault Dean was in this situation.

He shuffled into the kitchen and had just finished making coffee when Gabriel came out of his room.

“Morning, lil’ bro,” Gabriel greeted. 

Cas made no attempt at returning the greeting. Gabriel waited until they were both seated at their table and Cas had a few sips of coffee before trying to make conversation again. It was a tried and true fact that the younger sibling needed his morning coffee before the grumpiness subsided or at least subsided a little on rougher mornings. Gabriel could tell it was a rougher one and he knew why. 

“How’d it go in court yesterday?” 

“Dean was sentenced to two years. And he hates me,” Cas mumbled into his mug. 

“No way, I’m sure he doesn’t…” 

The glare when Cas looked up killed Gabriel’s train of thought and his attempt at cheering his brother up. 

“I have to go to work,” Cas said, getting up without finishing his coffee.

“Cas…” 

Gabriel had only been in a room with Cas and Dean once and Dean had been furious with Cas. However, from other stories Cas told him or the flowers he brought for their first date… no way Dean hated his baby brother. Even after everything that had happened.

Cas ignored his brother and walked into his room and shut the door. Pretending everything was okay at work was going to be nearly impossible but he didn’t have a choice. He took a deep breath and got ready for the day.

 

~~~

 

Dean was sent to Dixon Correctional Center in Dixon, Illinois. It was less than two hours away from Chicago so it would be easy enough for Sam to come and visit if he wanted to. 

Unfortunately, the bus that took a number of prisoners out there had a lot of familiar and unfriendly faces. Raphael, Uriel and Gordon were on his bus and he had heard rumors that some of the other guys were already in Dixon. Thankfully, Crowley’s trial was taking a while because he didn’t take a plea bargain and was going through a full trial so he wasn’t there. Yet. 

It wasn’t too hard for Dean to adjust to living in the prison. He had already been in lockup for over a week before being transferred here and it wasn’t much different. The food wasn’t too bad and the clothes were itchy. Nothing he couldn’t handle.

He planned to just keep out of everyone’s way, especially the guys he already knew, and to try to get that early release Moseley mentioned. Included in that plan would be to avoid getting on the bad side of his cellmate, Tiny. He was an ironically named huge guy that didn’t say much but Dean was learning to deal with him, too. All Dean had to do was to keep his smart mouth shut and not get on anyone else’s bad side. There were enough people in here already that wanted to kick the shit out of him.

After being in the prison for two weeks, Sam and Bobby came to visit him. A guard found him in his cell while he was reading Vonnegut and led him to the visiting area. Dean broke into a huge smile when he saw them. It was amazing to see familiar faces. It had been such a short time since he saw them in court but God, had he missed them. Dean really didn’t think prison would be so lonely.

He was allowed a brief hug with each of them before they sat down to talk.

“Hey guys,” Dean continued to smile, “great to see you.”

“You too, son,” Bobby said.

“How’s school, Sammy?” Dean asked, always the concerned older brother. 

“It’s fine, classes are good…”

“What about Jess?”

“We’re great,” Sam grinned, turning a little red. “I apologized and we actually have a date later this week.”

“Good for you, man,” Dean beamed, glad the two of them worked out their issues.

“What about you, Dean?” Bobby wanted to know.

“Me? I’m boring, it’s boring in here. But it’s fine. How’s the shop?”

“Fine?” Bobby repeated with raised eyebrows. “You’re in jail, what do you mean ‘fine?’”

“It’s not as bad as I thought and seriously I would rather talk about normal, outside life things right now, okay?” Dean said, a little rougher than he meant to sound. 

He knew Bobby was just worried about him and he appreciated it. There was honestly nothing to talk about though and he wanted to think about what was going on in the real world. 

“All right then,” Bobby agreed. “The shop’s fine. Sam here has taken your job.”

“Really?” Dean asked, thinking Bobby was joking.

“I suck at it but yeah,” Sam said, looking a little sheepish.

“Kid needed a job, I needed help in the shop,” Bobby explained.

“And what about Sam living on his own, did the court care?” Dean had to ask. 

Having your legal guardian convicted of a felony surely wouldn’t help a sixteen year old minor. Dean’s biggest worry when he went to jail was what would happen to Sam.

“They figured since I live in the building and he works for me that he’s being watched enough so that he can keep the apartment,” Bobby informed Dean. “Sort of a partway emancipated minor thing.”

Dean let a sigh of relief. At least that was something that didn’t go to shit because of this whole mess. 

“Thanks, Bobby,” Dean said.

The three of them kept talking about anything, mostly just trivial stuff, until they had to go. 

 

Dean had been in prison for four weeks when Cas stopped going to the GED classes with Pamela Barnes that he had been taking with Dean. He had been close to completing it but he just couldn’t find it in himself to finish without Dean receiving his own GED right next to him. All the plans they had together fell apart and Cas couldn’t handle being reminded of what he had lost every time he went and had an empty seat next to him. 

He just kept working and ended up talking more to Gabriel than he ever had before. Cas, without Dean, was spending more time at home and since he knew about Gabe’s involvement in Michael’s gang, the honesty kept flowing. That and just hanging out and actually feeling like brothers which Cas didn’t realize he had been missing so much. 

After a long talk with Gabriel one night after a particularly bad nightmare involving Crowley torturing Dean in prison, Cas came to a decision. It was time to face Dean and to talk to him. No matter how they ended or what Dean said, Castiel had to talk to him at least one time. 

Cas was going to visit him in prison.


	13. Chapter 13

Cas borrowed his brother’s old, gold car to go and visit Dean. He prayed it could take him the entire drive out there without dying. According to Gabriel it was a “pimp-mobile” which just made Cas uncomfortable but it was the only way he had to get out there. 

Once the two-hour drive was complete and Cas had signed in by registering his driver’s license and going through a metal detector, he sat and waited. The prison held pretty mild inmates so they could visit at tables in a room and talk face-to-face. A guard came back to him and told him that Dean Winchester didn’t want to see him.

“Are you sure?” Cas asked, feeling his stomach drop. He had feared their meeting would go poorly but he didn’t think it wouldn’t even happen.

“Yeah, I’m sure,” the guard rolled his eyes, “he didn’t want any visitor named Castiel Novak and we can’t make him unless you’re his lawyer. You his lawyer?”

Cas shook his head.

“Sorry, kid,” the guard sympathized.

Cas nodded and walked out. He was determined to talk to Dean eventually and make him understand. 

So he came back the following week. With both Cas and Gabriel working, it was hard to find a time that worked for him to take the car. Again, the guard told him Dean didn’t want to see him. 

This time, Cas gave it two weeks and it was now November. Same story but Cas was determined not to give up. 

Aside from these visits, Cas continued to work and actually talked more with Balthazar. As it turned out, Balthazar was aware that Cas was Gabriel’s brother the entire time because Gabriel was a little more talkative than Cas. The ride he gave him to the hospital to see Dean and the helpful texts were all to help a friend’s brother. Balthazar, like Gabriel, was somehow so under the radar that the cops hadn’t bothered arresting him.

Balthazar also now joined up with Gabriel to try to set Cas up on dates every once in a while but Cas wasn’t interested. Obviously, he wasn’t still in a relationship but he certainly was nowhere near over Dean. 

December came and gradually got later into the month. It was below freezing in Chicago and the lights all over the city were gorgeous but Cas didn’t notice. Despite his nonexistent holiday spirit Cas decided to visit Dean on the day before Christmas Eve. He hadn’t spoken to Bobby or Sam since Dean had been arrested and he didn’t want to. They would probably hate him more than Dean did, if that was possible. Cas’s best guess was that they would visit on Christmas Eve or Day so he wanted to avoid them at all costs. That would just be uncomfortable for everyone.

Dean, again, didn’t want to see him. 

Christmas with Gabriel was a lackluster affair. Castiel wasn’t in the holiday mood but still halfheartedly exchanged gifts and cooked a nice meal with his brother. He apologized for ruining Christmas and Gabriel pointed out that it wasn’t their worst one ever. Cas had to agree there.

Cas didn’t cry in front of Gabriel but did later as he was in bed. He thought of Dean in jail on Christmas, without Sam or Bobby, eating shitty food all alone and cried harder.

 

In the New Year, Cas made a resolution. He would visit Dean one more time but with a new idea that he got while spacing out at work. The next time, he was going to say he was Sam. Then Dean would come and talk to him. If it didn’t work, he would give up because if Dean kept saying no this many times to him meant that he really was over and done with him and nothing he could say would change his mind. 

He built up the courage for this crazy attempt and drove out on January 25th, the day after Dean’s twenty-first birthday.

Cas checked in as usual with his license. The next step involved a simple clipboard with the inmate name and the visitor’s name. Cas wrote that his name was Sam Winchester. Thankfully, it was a guard that had no previous contact with Cas who took the names to gather the prisoners. Cas sat and waited like he always did, more nervous than any other time.

“Winchester, you got a visitor,” the guard said, standing at Dean’s cell door as he read. He had gone through a lot of Vonnegut while was in there. 

“Yeah, who is it?” Dean demanded, not lifting his eyes off the page. 

“A Sam Winchester,” he answered after looking at his clipboard of names. 

Dean hopped up immediately and headed to the visiting area. 

_Sam was just here yesterday so something must be wrong, something must be very wrong_ … Dean thought. 

Something was wrong indeed. It wasn’t his brother but Cas sitting at the table waiting for him.

“You’ve got to be fucking kidding me,” Dean said, looking Cas in the eye. He turned and tried to leave but the guard who got him from his cell forced him to have a seat across from Cas.

“Seriously? You pretend to be Sam? I thought something was wrong, damn it!” Dean snapped, his voice almost a yell.

“Keep it down, inmate,” the guard snapped.

“I’m sorry Dean but this was the only way you’d see me,” Cas said, looking down with guilt. 

“Yeah, take a fucking hint, man. I didn’t want to see you the first however many times, why would I want to now?” Dean said, still with an icy edge to his words. 

Cas looked up and got a good look at Dean. He looked exhausted and defeated with bags under his eyes, one which was freshly black, and some bruises on his face. 

“Dean…”

“Oh, my face? I look beat to hell because of the guys in here who constantly take their anger out on me because of you.”

That was a blow to Cas’s gut. 

“I never thought…” He was going to say he never thought it would get so bad in here but Dean interrupted.

“No, you didn’t think. You thought about yourself and _your_ brother. Well, what about me? And my brother? Now, Sam had to come all the way out here to celebrate my birthday with me in friggin’ jail. Not exactly how I pictured my twenty-first going,” Dean said angrily. 

“I’m sorry, none of this was supposed to happen. I tried to keep you out, to keep you safe. When we skipped selling, remember? But Crowley dragged you back in and Mills and Henriksen didn’t give me a choice,” Cas tried to defend himself, his voice small.

“You had a choice but you made the wrong one. You should have fucking told me! Instead of lying and getting me stuck in this shithole,” Dean said, his voice elevating to a yell. 

Dean stood up suddenly and stormed to the door where he came in. The guard was ready to let him pass but Cas stopped him.

“Dean,” Cas said, standing up. He put as much pleading and desperation as he could put in one syllable.

It worked because Dean turned around. 

“Falling in love with you wasn’t supposed to happen,” Cas explained again. “I still love you, Dean.”

Dean scoffed and Cas’s stomach clenched and he felt cold. Dean was looking at the ground and shaking his head before he looked up.

“You know what the worst part is, Cas?” Dean asked.

Cas’s mouth went dry. It hurt to hear him say his name like it tasted wrong and he wasn’t sure he wanted to know.

“The worst part is, I still love you too.”

 

~~~

 

A miserable January slowly became a dismal February. Castiel hadn’t tried to visit Dean again and he wasn’t planning on doing so anytime soon. It was hard not to give up when they both still loved each other and were willing to admit it but Dean wasn’t ready to forgive him. Cas wasn’t sure if he would ever be able to. 

Gabriel and Balthazar were trying to help in their own way. It mostly involved dragging Cas to parties were he was cordial to everyone he met but it just felt wrong. How could he party while Dean was locked up? He honestly couldn’t picture himself with anyone other than Dean and every person he met reminded him of what he had lost. 

On the first of March, Gabriel decided to sit down and have a talk with his brother. He understand what had happened and the two loved each other but the gray cloud following Cas around was infectious in the worst way. Gabriel wanted to help his little brother past this whole ordeal. 

“Cassie, can I talk to you?” Gabriel asked, plopping on the couch next to Cas. Cas had a show on but he wasn’t paying attention.

“It seems as if you already are doing so,” came Cas’s dry reply, his eyes not leaving the TV. Gabriel rolled his eyes on the inside but kept a concerned look on the outside.

“Look, I know it’s been hard for you lately and I…”

“You think I can just move on, sleep with random people and drink to feel better like you and Balthazar do?” Cas snapped, turning his head to face Gabriel. He knew he was being unfair but he couldn’t help it. "It was hard enough trusting Dean, to be intimate with him. I've never felt like that before and I don't know if I ever will again."

“Of course you will. Give it time and maybe stop moping around,” Gabriel said. His voice was genuine and he clearly wanted to help, Cas knew that, but it was hard to hear. 

“I just… I can’t, Gabriel,” Cas sighed. “I have tried moving on but I can’t.”

In contrast to his usual chatty self, Gabriel kept quiet. Time was the only thing that would help.

 

In the middle of March, Dean was woken up one morning and immediately swung a fist. He had grown accustomed to being attacked right he was woken up by his former gang members and occasionally their rivals. 

“Hey, easy brother,” came the startled, Southern drawl.

“Benny?” Dean asked, sitting up and rubbing sleep out of his eyes and letting his heart rate settle. 

“Yeah, man!” was the answer from Benny. Sure enough, the guy was standing right in front of him.

“What the hell are you doing here?” Dean asked in disbelief. He was supposed to get away and to be with Andrea. 

“They finally caught up to me, I guess,” Benny explained.

It was nice to finally have a friend and ally in the prison that Dean was almost happy before realizing how much this would suck for Benny.

“What about Andrea?” Dean asked. 

“She’s fine. Pissed, but…” Benny looked down. “We’ll see.”

Dean nodded. The two of them went to play some checkers in the rec room. That was where they found who else came in with Benny.

Crowley.

“Shit, Benny, you didn’t mention Crowley was here!” Dean said, dragging Benny away from that room.

“Oh yeah,” Benny shrugged.

“That’s it? They’ve been giving me hell for five months! Him being here is going to make it worse and they’re going to hurt you too, man. We’re way outnumbered.”

Benny didn’t say anything as they walked away and went to go anywhere Crowley wasn’t.

 

Sam and Bobby visited Dean the next day.

After their usual hugs and greetings, they all sat down.

“Nice shiner, Dean,” Sam smirked. 

He did have quite the black eye since Crowley had found him. He had brought Jake and Gordon and Benny had been somewhere else when it happened.

“Shut up,” Dean said but with a smile. No need to be mean to Sam or let him worry. 

Dean asked Sam to get him something from the vending machines. It was a rare occasion for Dean to get junk food. Sam listened, feeling a little bad for the poke at Dean but that’s what brothers were for. 

“Bobby, I gotta ask you a favor, man,” Dean asked when Sam was out of earshot. 

“Anything,” Bobby agreed. 

“Stop bringing Sam here,” Dean pleaded. Bobby looked confused. “He needs to focus on school, his girlfriend… having a normal life. He doesn’t need to keep coming in here and seeing his fuck-up brother.”

“Listen to me, boy. You are not a fuck-up. You did what you had to do,” Bobby said. Dean nodded at the sentiment but didn’t believe him. 

Sam sat back down with a bag of Cheetos for Dean.

“So, Sammy, how’s school?” Dean asked while ripping into the bag.

“Fine, fine,” Sam answered. “Jess is too before you ask.”

“You both still looking at college and getting ready for ACT’s or SAT’s whichever they make you take?” Dean wondered. 

“Yeah, she wants to go to Stanford, too! Get this, her dad went there and she’s always wanted to. It’s perfect!” Sam beamed. 

“That’s great, Sam!” Dean grinned. 

It was nice to hear some good news. It would tear him apart to not see Sam but he couldn’t hold him back anymore. Sam needed to focus on himself and be successful all on his own. One Winchester had to make it in this shitty world. 

 

At the beginning of April, Dean got a letter from Sam explaining why he hadn’t been able to visit. According to the letter, Bobby’s garage and Ellen’s bar were under investigation in connection to Crowley’s gang. It would look bad for Bobby to visit and Sam couldn’t visit without an adult. 

That was practically a relief. With this, Bobby had an excuse to not bring Sam around. There was no proof anywhere that Ellen and Bobby had anything to do with what had been going on. Besides the guys frequenting the bar and Dean working for Bobby, there was no connection and everything would be fine. Nothing could tie them to their illegal activity except….

Dean sat up on his lower bunk so fast he hit his head.

_His gun._

Dean immediately jumped off of his bunk and ran to the phones as fast as the guards would allow to call Bobby about the gun he had hid in his garage so long ago, ignoring the swelling of the bump from where he had hit his head. 

The phones were full when Dean ran up to them. _Of fucking course_ , he thought, _just my luck._

He picked the smallest and least intimidating guy and ripped the receiver from his hand, clicking to end the call. 

“Hey, I wasn’t done!” the guy protested. Dean towered over him and glared.

“Yeah,” Dean stated matter-of-factly, “you were.” The other guy scampered away. 

Dean dialed Bobby’s number from memory and he answered after the third ring.

“Dean?” 

“Bobby, hey, Sam wrote me a letter, saying you’re under investigation so there’s something you need to know…”

“I already took care of it.”

“What?” Dean asked. That was about the last response he was expecting. 

“You think I don’t know my own garage, ya idjit? I saw your gun right away. Fool move putting it here without telling me,” Bobby said. 

Dean could hear his eye roll over the phone but almost laughed. Of course Bobby took care of it. He wouldn’t be Bobby if he wasn’t on top of his game. 

“Jeez, Bobby, I’m sorry. I wasn’t thinking…”

“Do you ever?” Bobby sighed. “I get it, you were in a hurry. It’s fine. Everything’s fine.”

Dean let out the breath he had been holding. From what Bobby said, he could rest easy knowing he and Ellen weren’t getting dragged under because he was stupid and fell in love with an informant of all people. 

“You and Ellen good then?”

“Yeah, they can’t prove a damn thing. We’ll be all right,” Bobby said.

“Have you… talked to Lisa?” Dean asked with trepidation. He knew it was foolish to have Bobby bother her but he wanted to stay in touch. 

“Yeah. I’m sorry, boy, she doesn’t want to visit you. Doesn’t think it’s a proper place to bring a baby.”

“I get it. I mean…just, if it’s mine? I would want to meet him, you know?”

“I met the little guy,” Bobby said, “when I talked to her.”

“Yeah?” 

“Cute little thing. She named him Benjamin Isaac.”

They didn’t talk much more after that. Dean had changed the subject to Sam for a second then he said a quick goodbye to Bobby to let him get back to running his garage.

 

~~~

 

It was soon May and Cas found it hard to believe that he had met Dean almost a year ago and that he hadn’t talked to or seen him in four months and that everything had changed in the course of one year. He would have traded pretty much anything to hear a sarcastic remark from him or to touch him. Anything to remind him of what they had. 

Cas was walking into a diner with Gabriel and Balthazar, not Benny’s because it held too many memories, when they ran into Sam and Jess who had been on their way out. 

Cas had almost missed him because he had been rolling his eyes at something that one of them had said when he heard his name. 

“Cas?” 

“Hello, Sam,” Cas greeted, bewildered at seeing him. Gabriel and Balthazar went into the diner and Jess went to wait in the Impala that was parked on the street next to where Sam and Cas stood. 

“How’ve…uh, how are you?” Sam asked, a little awkward. Castiel was glad that it didn’t seem as though Sam hated him, which was a good sign.

“Good. I see you and Jess have worked things out,” Cas observed, nodding towards her. 

“Yeah, we’re great. Our junior year is almost over, can you believe that?”

“It’s hard to believe you had just had gotten your license at about this time last year,” Cas said with a small smile. 

Both of them recalled the night that Sam had come to pick up Cas and Dean after Crowley’s party had been busted. The conversation stalled for a second because neither of them knew if talking about Dean would be a good idea. 

“You must be seventeen now,” Cas changed the subject.

“I am, birthday was last week.”

“Happy belated birthday, Sam.”

“Thanks, Cas,” Sam said, with a slight smile. “So, what have you been up to?”

“Just work, mostly. Hanging out with my brother and his friend a lot,” he paused. “The car looks good.”

“Yeah, he’d kill me if…” Sam started. 

Cas looked down and Sam cleared his throat.

Sam glanced at the car, remembering Jess.

“It was good to see you Cas, really, but I should go.”

“Yeah, it was good to see you too, Sam.”

Sam gave him a nod and walked around to the driver’s side of the car. Memories of Dean doing the same thing flooded Cas’s brain and he almost didn’t say what he wanted to Sam because of the distraction. 

“Sam,” Cas called from the sidewalk.

Sam paused with the door open. 

“Sam, I just wanted you to know… I’m sorry. For everything.”

“I know,” Sam nodded again and got in the car.

Cas still felt guilty about the whole thing but was relieved that at least Sam didn’t hate him. He joined Balthazar and Gabriel in the diner. 

 

“And her name is April, real nice, smokin’ bod…” Gabriel was going on. Cas was looking out the window.

“Have you heard anything we’ve said?” Balthazar asked.

“Something about a girl named April, I believe,” Cas answered, looking down at his barely touched food. 

“Yes, you have a date with her next weekend. You’re welcome,” Gabriel explained.

“What?” Cas asked incredulously. The meddling older brother act was getting old. 

“Yup. It’s happening. You’re getting back out there.”

Cas didn’t say anything and just pushed his food around on his plate. Sure, they could set him up on dates and maybe he would even go but it wouldn’t change anything. Cas was still in love with Dean and going on a date with some girl wasn’t going to change that.

 

Cas did in fact go on the date a week later. Gabriel had suggested the simple dinner and a movie routine and despite that being what he and Dean did on their first date, he figured it was the best option. He even copied the flowers idea and bought some on his way to pick her up in Gabriel’s car.

The date was fine, April was nice enough, but it just felt friendly to Cas. There were no butterflies or an urge to kiss and to touch like when there had been with Dean. The spark just wasn’t there. At all. He always had been reserved and didn't feel sexual attraction often, but he didn't even feel potential with her.

On their second date to the Museum of Science and Industry, April picked up on the fact that Cas was way more interested in the exhibits than in her. Cas just kept looking at the cool machines and the explanations of how it all worked and he knew Dean would love it. He was so caught up in that and wishing Dean was there that he had been inadvertently ignoring April. It got so bad that she said something about it. 

“What? No…” Castiel protested but he knew it was weak at best. April gave him a knowing look.

“I’m sorry, I know this isn’t fair to you. I’m still getting over someone.”

“You’re brother mentioned that when he set us up,” April said with a smile. She, thankfully, didn’t seem upset and was very understanding. 

So it was over as quickly as it had begun, much to Gabriel’s dismay.

“Did you even try?” Gabriel questioned when he got home from the ill-fated date. Cas’s raised eyebrows answered that question easily. 

Following that, Gabriel had backed off. He figured if new love was to find his baby brother, it would happen on its own. 

 

Without Gabriel’s intervening, Cas had the most boring summer of his life. He didn’t notice the flirting of a new coworker because when he wasn’t reshelving books or helping someone find something, he was behind the help desk writing. The variety of people that passed through the library gave him plenty of material to work with. That was when people did come in. The summer was never very busy.

The sad thing was, this summer was exactly like two summers ago, the one before Dean. But now he knew how exciting life could be and what being in love was like and the subsequent heartbreak. The saying ‘you don’t what you got til it’s gone’ never rang more true to Cas than it did during those summer months. 

Once the school year began again, Cas’s workload in the library picked up a little but not enough that he didn’t have time to have a night in with Gabriel, Balthazar, beer and pizza every once in a while. 

September started and Cas received a text from Sam asking if he wanted to meet him at the Roadhouse, just to talk and catch up. Castiel didn’t know if it was the best idea but he agreed. 

That was how Cas found himself back in the familiar bar that had somehow become so foreign at the same time. Cas sat at one of the small tables and Sam showed up a couple minutes after him. Ellen came out of her office to say hi once Jo knocked on the door.

“Hi, boys,” she greeted. “What can I get you?” 

Cas didn’t feel drinking so they just each got a soda and a plate of fries to split. 

“Well, I’m glad she doesn’t hate me,” Cas said with relief.

“Of course she doesn’t!” Sam exclaimed, seeming shocked that Ellen would hate anyone. Dislike or be stern with, sure, but hate was something else entirely. 

“I got the guy who is like a son to her arrested and her bar scrutinized by authorities. She has every right to hate me,” Cas said, looking down at the table. 

“Well, she doesn’t. Neither do I or Bobby,” Sam assured him.

“What about Jo?” Cas asked with a nervous glance behind the bar. “She looks mad.”

“She always kind of looks mad,” Sam said with a little laugh. “She’s overly protective of Dean, you know that.” 

Cas nodded and hoped she would forgive him like, luckily, almost everyone else had seemed to. Cas knew he didn’t deserve it and he understand more and more why Dean was so grateful for this wonderful family. He also didn’t talk about Dean hating him because he got that message loud and clear without asking.

“So, senior year, are you excited?” Cas asked, changing the topic. 

“Very. Already began work on my application to Stanford and so did Jess. Fingers crossed,” Sam grinned as Ellen brought their food out.

“Enjoy, guys,” she said, placing the plate and cups down.

“Thanks, Ellen,” Cas said, thanking her for more than just the food. Ellen smiled before heading back to the office. 

Sam and Cas talked about little stuff, avoiding the topic of Dean, for a solid hour until Sam had to go pick up Jessica for a study session.

Outside the bar, the two paused. 

“Do you want a ride?” Sam asked, holding the keys to the Impala in his right hand. Dean’s baby was parked in front of the Roadhouse. Memories of making out on the hood of the car multiple times and in the front seat flashed in his mind. He couldn’t be in that car. Not yet and certainly not without Dean driving it again. 

“I’m all right to walk. It’s a beautiful day out,” Cas said. Sam looked skeptical but agreed. They said goodbye and went their separate ways. 

 

~~~

 

Cas had just gotten home from work on a day in the middle of October. It had gotten colder so he changed into sweatpants and made himself some tea. He had just sat down on the couch with his tea and a book when the front door flew open with a bang.

“OW!” Cas yelled, spilling hot tea in his lap, ready to go off on his brother. “Gabriel…what the…”

Gabriel seemed out of breath from running and seemed a little panicked. 

“Cas…won’t believe… holy shit…car…he…”

“You’re not making sense, Gabriel. Sit down,” Cas ordered. 

Gabriel sat on the couch and tried to catch his breath. Cas placed his book down and walked to the kitchen to place his mug in the sink and wipe himself off with a towel. He got a glass of water for Gabriel and walked back over.

“Drink. Slowly.”

Gabriel did and his breathing got closer to a normal level. 

“Now, try again. Tell me what is so wrong you had to scare the shit out of me.”

“Language, wow little bro…” Gabriel started but was cut off by a stern look from Cas. 

“All right, all right,” Gabriel said before taking a big, deep breath and continuing. “I was driving my car and you know it’s not reliable at all. Well, the gas was half full, engine was fine I thought and I still had a while until my next oil change. Probably. How many miles is it between oil changes?”

“Gabriel,” Cas snapped. “Focus.”

“Sorry. The car broke down. So I got some guys to help me push it to the nearest auto shop. Guess which one it was?”

“Singer Auto?” Cas asked, judging by the sly grin on his brother’s face. “And?”

“Well, the owner just so happens to have his favorite worker back,” Gabriel said with a huge grin. Cas wasn’t following. He squinted and tilted his head to the side.

“I’m talking about Dean, Cas,” Gabriel said, exasperated. “Dean is back.”


	14. Chapter 14

Castiel didn’t know what to do. No one told him Dean was back. Sam could have, they had stayed in touch since meeting at the Roadhouse. Or Ellen or Bobby. Hell, Jo could have said something. Surely, they all knew. It couldn’t have been a surprise to any of them that Dean had been released from jail.

“Castiel!” Gabriel shouted.

“What?” Cas asked, confused why his brother was suddenly shouting. He sat down in the armchair next to the couch.

“I asked you a question,” Gabriel rolled his eyes. “Are you going to see him?” 

“I… I don’t know. Should I?” 

“Of course! Hop on that boy of yours! Literally. Go down to that mechanic shop so he can get his hands off the auto bodies and onto yours,” Gabriel finished with an eyebrow wiggle. 

“Please,” Cas scolded, “be serious.”

“Oh, I am serious. Go get him!” 

Cas sat in continued shock and planned a course of action. He wanted to see Dean and talk to him, of course, but would Dean want to see him? It had been nine months since he had last seen him but felt like yesterday. Cas ran that entire conversation through in his head at least once a day. It was eating at him until they could have a better talk and this could be his chance.

“Well when you figure it out let me know. I gotta go,” Gabriel got up off the couch and back out of the apartment. 

Cas barely registered that Gabriel had left. He pulled out his phone and held it in his hand. The best course of action would be to text or call but he wanted more than anything to run down to Singer Auto and kiss Dean but he knew that wouldn’t happen. Dean would probably not even want to speak to him let alone kiss him. 

After he spun his phone around in his hand several more times, he created a blank new text message addressed to Dean. Briefly, he worried if Dean would still have the same number. He didn’t dwell on that because if he thought about it too hard he would use that as an excuse to chicken out and not say anything. 

He took a deep breath and started to type.

Cas: **Gabriel said he saw you at Bobby’s garage.**

He hit send before changing his mind. Five minutes passed of Cas staring at his phone until it finally buzzed with a response. Cas’s stomach flipped.

Dean: **Saw him too.**

Cas wasn’t entirely sure how to respond. It was a choppy answer and one that didn’t leave room to expand the conversation. 

Cas: **So you’re out.**

Dean: **Seems like, yeah.**

Cas blinked at his phone a couple times. It was hard to get a read on Dean through texting and now Cas wasn’t sure what Dean was thinking. A year apart is a long time.

Cas took ten more minutes before saying something else. 

Cas: **Should we talk? Or can we?**

Dean: **I don’t know if that’s a good idea.**

Cas’s heart sank but he answered anyways.

Cas: **It would help clear the air on things**

Dean: **Fine.**

Cas: **Dinner?**

He knew it was a bold suggestion instead of just meeting at one of their apartments or going for lunch or coffee instead. Dean took a while to respond and Cas thought he might have pressed his luck too far already.

Dean: **Fine.**

Cas got a flutter of excitement through his entire body that he hadn’t felt in a long time. God, he had missed that feeling. Even if Dean was mad, Castiel got to sit across from him and have dinner with him. God, just to hear his voice would be amazing. 

Cas: **Tomorrow at Giuseppe’s?**

Cas knew it was even more bold suggesting they go to the restaurant they had their first date at if they were trying to keep it casual but he had to try.

Dean: **Yeah. But we drive separately and keep it quick.**

Cas: **Okay**

Cas wasn’t really okay with that, he missed Dean’s car and how Dean looked driving it, but he felt like he had to agree. Letting Dean set the terms would help him feel more comfortable and this was more than enough. Cas knew he didn’t really have a right asking anything of Dean at all after everything he had done.

~~~

The next day, once Gabriel finished being ridiculous and running around the apartment with excitement like the kid on a sugar high he was on the inside, he gave Cas the keys to his car. 

“No sex in my car,” Gabriel said as he handed them over.

“Ha ha,” Cas said without humor, knowing that was so far from happening.

As he drove to the restaurant, he almost rear-ended a car because he was so distracted. And nervous. He hadn’t seen Dean in months and worried how he would be different or would think Cas was different. Cas also wasn’t sure if Dean had begun to forgive him at all. Chances were not likely.

Cas parked and walked in and found Dean right away. The first thing Cas noticed was that Dean seemed a little more toned but otherwise looked the same.

Cas smiled as he walked up. 

“Hello, Dean,” Cas said as he sat down.

“Hey, Cas,” Dean answered, one side of his mouth twitching into Cas was hoping was a smile.

So far, so good, Cas thought. 

“You look good,” Cas said without thinking. It was true and it was out of Cas’s mouth before he could stop it.

“Cas, don’t,” Dean sighed.

“Don’t what?” Cas asked, confused. It was the honest truth and he had missed Dean so much.

“Never mind,” Dean said. There was an awkward silence where they both drank their water. The waiter came and took their drink orders, both of them getting pop.

“So, you’re back at work,” Cas stated. Dean laughed a little. Cas had missed that sound so much and he had to smile.

“Yeah, as soon as I got back last week, Bobby gave me my job back,” Dean shook his head. “Sam had my job while I was in… while I wasn’t around. He said Sam was just terrible at it. Doesn’t know cars like me. Or like my dad did.” 

Cas paused then tilted his head to the side as he thought of something. 

“Last week?” Cas asked.

“Um… yeah,” Dean answered, shifting in his seat.

“You didn’t tell me,” Cas accused.

“I didn’t know if that would be a good idea,” Dean shrugged. “We didn’t part on the best terms last time.”

“No, but that was a while ago, Dean,” Cas said. They took a pause in the conversation to order their food when the waiter came back with their drinks. 

“Yeah, it was but… I mean, we’re not together anymore,” Dean pointed out. Cas knew that but having it said out loud hurt.

“But we’re fine now, just talking. I missed you and I don’t want to not have you in my life. I’ll take as much as you’re willing to give. Anything is more than enough,” Cas said quickly. He spilled it all and let Dean process it and he just nodded. 

The conversation stayed a lot lighter after that, mostly small talk. Cas told Dean about work and what he had been up to as they ate. It felt familiar and foreign at the same time. The conversation was cordial but almost too much like they were both ready for something to go wrong.

“Gabriel actually set me up on a date,” Cas said. Dean nearly choked on his food and paused to take a drink.

“Really?”

“Yeah. We went on two but the second one was to the Museum of Science and Industry and I just kept thinking about you and how much you would love everything. We should go sometime.”

“Cas,” Dean sighed. “You can’t say things like that, all right? We’re taking it slow here. Whatever this is now has to be very slow.” 

Cas said he understood.

Once they finished, Cas insisted on paying. 

“I think I owe you a lifetime of favors. Let me pay for dinner,” Cas said when Dean started to protest.

“Fine. But you know it’s not a date, right?” Dean reminded him but with a little smile. 

Cas nodded. he understood Dean couldn’t just forgive and forget and let everything go back to normal. But he was serious when he said any time at all with Dean was plenty and more than he deserved. 

Outside, they were about to split up and head to their cars. They said goodbye and Dean started walking away.

“Dean,” Cas called. Dean turned around.

“Yeah, Cas?”

“Did you mean what you said? At the prison?” Cas asked, remembering the last thing Dean had said to him nine months ago about how he still loved him.

“Every word.”

 

Dean got home after dinner with Castiel and immediately went to the kitchen cabinet to grab the whiskey. Sam was at the table doing homework and raised his eyebrows but didn’t say anything. 

“It went that well?” Sam asked as Dean laid down on the couch. 

“It was fine,” Dean sighed. “It’s just…”

“Just what?” 

Dean pulled from the bottle, closing his eyes as the alcohol’s familiar burn met his throat. A year without this crutch had been pretty hard. He constantly had headaches and shaky hands his first month in jail from having no alcohol or cigarettes. The drinking he started up again but he figured he could do without the smoking.

“How did Jess and you work everything out?” Dean asked carefully. He understood this was still a sore subject.

“I understood that I had messed up and I had practically begged for a second chance and apologized. A lot,” Sam said. The two of them had recently turned in their early admission applications to Stanford and were waiting to hear back. 

Dean kept his eyes closed and thought about Sam had said. Cas had apologized, several times, but it was difficult. It was difficult to begin to forgive someone who got him arrested and then sent to jail for a year. Especially if he was still frustratingly in love with him. It was impossible to stop loving Cas and tonight did him no favors. Talking to him, seeing him, just brought all his old feelings back but he couldn’t act on them. It was too soon and he hadn’t forgiven him yet. 

Dean drank again. 

“So, what’s up with you and Cas then?”

“I don’t know,” Dean shrugged. “We talked, it was fine, but it’s hard to forgive what he did.”

“Dean, you know how bad he feels.”

“Yeah, that may be. But he could have gotten you sent to a group home or foster care or something if we didn’t have Bobby. Bobby or Ellen could have gotten into trouble. Benny lost Andrea, did I tell you that? She already wants a divorce. Everything went to shit. I can’t just let that go,” Dean said, sounding empty and sad. He brought the whiskey back to his lips. 

“True. But I’m fine and so are Bobby and Ellen. The garage is good and so is the bar. We’re all fine, those are just what-if’s. And while it sucks that Benny and Andrea are splitting, you know how they were. You told me they fought all the time. I doubt it would have lasted anyways,” Sam reasoned. 

Dean looked at his brother. “You really have an answer for everything?”

“Mostly, yeah,” Sam grinned. 

“So, what about Lisa? I’ve never met her kid that might be mine, in case you forgot, because she didn’t want to bring him to the jail. What’s your response to defend Cas there?” Dean asked. 

He didn’t want to snap at Sam but maybe he was trying to find an excuse to stay mad at Cas and he didn’t know why.

“First, you don’t even know if that’s your kid, Dean. Second, you can visit the little guy now. He wouldn’t have remembered anyways,” Sam rationalized again. Dean didn’t answer because the whiskey was again at his lips. 

“You still love him, don’t you?” Sam said.

“Yeah,” Dean admitted.

“Then what’s stopping you?” 

“He hurt me before. What if he does again, Sam?” Dean asked. 

“He made a mistake. You really can’t expect anyone to be perfect. But I know he would never hurt you again,” Sam said.

“You’re pretty smart, Sammy,” Dean said with a small smile. He said good night to his brother and took his bottle of whiskey to bed.

There was no way he wouldn’t think about Cas as he fell asleep because he always did. 

 

~~~

 

A week after the dinner and brotherly chat, Sam came running into the apartment holding a piece of paper. 

“DEAN!” Sam called. Dean stepped out of his room.

“What is it Sam?” Dean asked, worried something was wrong. Then, he saw the letter in his brother’s hand.

“Is that…is that it?” Dean asked hopefully.

“Yeah, I read it on the stairs coming up. I got in Dean! Full ride!” Sam said, beaming ear to ear. 

Dean smiled bigger than he had in over a year and that wasn’t an exaggeration. He pulled his little brother into a bone-crushing hug.

Sam called Jess and found out that she also had gotten her acceptance letter and got in. Sam couldn’t stop smiling as he walked out of the apartment to see if Bobby or Ellen or Jo were home to tell. 

Dean sat on the couch and waited for his brother to return. He wished, like he usually did, that his mother was still alive. She would have been so proud. 

Dean considered texting Cas. Since their dinner they hadn’t seen each other but they had texted over the weekend briefly, still moving slowly and becoming sort of like friends again.

Once Sam came back in, Dean gave him another hug.

“I am so proud of you, Sammy,” Dean grinned.

“We should all go for ice cream,” Sam suggested.

“Sure. Who do you want to come?” Dean asked.

“Well, us two and Jess of course. Bobby, Ellen and Jo are all working tonight I just found out. How about Cas?” Sam finished, tentative with the last suggestion. 

“Are you sure?” Dean asked.

“I mean, if it’s okay with you. We talked a few times while you were gone and we’re friends but it’s up to you.”

“It’s your big day here, if you want him there I can call him,” Dean asked. 

He wasn’t going to be a high school girl about this. If Sam wanted Cas there, it would happen. It was obviously not a double date and he had made it clear to Cas where they stood. Sam said he would like Cas there.

So Dean called Cas who said he would love to help Sam celebrate. Dean and Sam got into the Impala and drove to pick up Jess and then Cas. 

“You sure you’re okay with this?” Sam asked, distracting Dean from focusing on his baby. He didn’t think he would have missed his car so much. Luckily, Sam had taken good care of her.

Well, besides the iPod dock Dean had removed immediately. 

“Of course. Wouldn’t have called him if I wasn’t,” Dean said, his eyes not leaving the road. 

He remembered the last time they had gone to ice cream when Jess and Sam had started dating last summer. Dean had driven Cas home and had kissed him.

He didn’t have time to dwell on that anymore once Jess and Cas were in the car. Besides a quick hello, Cas and Dean didn’t say anything and let Sam and Jess carry the conversation. They got to the ice cream shop and decided to eat inside since it was getting cold out. 

It was nice to just sit and celebrate Sam and Jess and all they had accomplished. The pressure from when it was just Dean and Cas wasn’t there and it was easier.

“You must be really proud, Dean,” Cas said softly so only he could hear. At the other side of the table Sam and Jess were talking about something else.

“I am,” Dean smiled. Cas smiled back and it felt intimate and like it used to until Dean coughed and turned to get back in the conversation. 

The rest of the time in the shop was fine. Once they were outside the car, Sam asked if he and Jess could be dropped off at a movie theater close to where they lived. They climbed into the back and Cas moved to shotgun. 

After the happy couple was out of the car, there was a pause before Cas filled it as Dean drove towards Cas’s apartment to drop him back off.

“He’s quite the kid,” Cas pointed out.

“Don’t I know it,” Dean grinned. “How’s your brother?”

“Annoying but mostly lovable, his specialty.”

Dean laughed a little and looked sideways at Cas who smiled back. Dean looked back to the road.

“You did that at ice cream, too,” Cas said.

“Did what?”

“Looked and then looked away like… I don’t know.”

“I have to look at the road!” Dean argued.

“You know what I mean,” Cas insisted. Dean did know what he meant but sighed.

The Impala rolled to a stop in front of Cas’s building. 

“Cas, you know I care about you a lot. But if we do ever go back to what we were, it’s going to take some time,” Dean said, turning to look at Cas. “Might be a while, I don’t know.”

“I understand, Dean,” Cas said.

“I just… I can’t get hurt again, you know? You…”

“Dean, I am sorry,” Cas said, reaching his hand out to grab Dean’s hand out of a long lost habit. “I will never hurt you again, you have to believe me.”

Dean’s eyes were on their hands as he nodded. When he looked up, Cas had leaned in and squeezed his hand before kissing him. Dean sighed into the kiss and took a second to react before kissing Cas back. Then, it was over suddenly and Cas looked terrified.

“I…I’m so sorry, Dean,” he said, his eyes huge. He got out of the car and into his building before Dean had a chance to say anything, the ghost of the kiss on his lips.

 

Castiel ran all the way to his room and he shut the door to avoid Gabriel, sliding to the floor against it.

 _How could I be so stupid?_ Cas thought bitterly. _That was too fast, now Dean isn’t going to want to spend time with me at all and that’s all I want._

Cas spent five more minutes thinking of everything he should have done instead. He finally got up and decided to get ready for bed even though it was only about eleven.

After he came back into his bedroom after using the bathroom, his phone had a missed call. It was from Dean. Cas didn’t know why Dean would even want to talk to him ever again but he called him back anyways.

“Hello?” Dean answered. 

“You, uh… called?” Cas asked, scared that Dean was going to go off on him for overstepping…

“Are you okay?” Dean asked. That was not what Cas was expecting. He stopped pacing around his room.

“What? Me? Dean…”

“Yeah, you ran out in a panic. Are you okay?” Dean repeated. 

“I…I’m fine! I thought…” Cas paused, sitting on the edge of his bed.

“Thought what? I’d be mad or something?” Dean asked, still able to read Cas’s mind after all this time. 

“Well, yeah,” Cas admitted.

“I’m not. Honestly, Cas… you’re still as ridiculous as always,” Dean said and Cas could hear his smile over the phone. “Of course I’m not mad but…”

“It was too fast?” Cas guessed, still able to read Dean’s mind.

“Yeah. But that doesn’t mean that it wasn’t nice. I mean… I missed that. And you. But we just have to slow down,” Dean explained. “I just need time.”

“So, we can hang out again?” Cas asked tentatively. 

“Yes,” Dean laughed, making Cas laugh too.

“All right. I’d like that,” Cas said.

“Good night, Cas,” Dean said.

“Good night Dean,” Cas answered. 

He let out a deep sigh before laying down and he fell asleep with a huge smile on his face. It was the best night’s sleep he had gotten in over a year. 

 

~~~

 

The rest of October and the first half of November, Cas and Dean began spending time together again. It was like when they had first started hanging out, a little bit of tension and awkwardness but it was nice.

Cas was sure to keep things slow, like Dean had with him in the beginning, even though he wanted to kiss him every time he saw him. He put a lot of effort into not reaching around Dean’s waist to hold him while he made food for the two of them and Sam or to reach out and hold his hand while he drove them somewhere. Hopefully, he could do that soon and it was worth it to wait.

Dean had been back for a month and Sam had not so subtlety been trying to get him to spend more time with Cas and get the relationship back to what it was and Dean was trying. Slowly but surely, his walls were breaking down. 

“Cas, what are you doing for Thanksgiving?” Dean asked while they were sitting on the couch watching a movie with a friendly amount of space between them. It was the Monday before Thanksgiving. Since it was break for the schools, Sam and Jess were… somewhere. Dean just knew it gave him the apartment alone with Cas. 

“Probably spending it with Gabriel and Balthazar. How about you?” Cas asked, turning to face Dean.

“Just here or Bobby’s. Me, Sam, Bobby, Ellen, Jo…maybe Jess after she eats with her family,” Dean said, looking like something was on his mind. “Would you guys want to join us?”

“After everything that went on between you guys?” Cas asked, specifically thinking of Gabriel helping to beat Dean up.

“Oh, that’s water under the bridge,” Dean smirked, “and I want you there. So, if they’re part of the deal, so be it.” 

“I’ll ask them. I’m sure they’d love to come,” Cas said with a smile. It was maybe an exaggeration but if Cas asked nicely, they would come. 

“So, you want me at Thanksgiving. You’re sure that’s not too…” Cas didn’t finish because Dean had moved and closed the space between them on the couch. 

“Dean…” Cas said softly. 

“I did say slow not never,” Dean smiled. His eyes flicked to Cas’s lips before he kissed him. 

They were so distracted by kissing, Dean moving to be over Cas, that they didn’t hear the front door open.

“Oh, come on, guys!” Sam exclaimed as he came into the apartment. Dean quickly got off of Cas, both of their faces very red and lips a little swollen. 

“I would apologize but…” Dean said with a smile, Cas nudging his arm but also smiling.

“Yeah, of course you’re not sorry,” Sam said, smiling and shaking his head. He would suck it up and take the scarring images if it meant seeing these two happy again.

 

Thanksgiving arrived a few days later, Cas showing up at Dean’s apartment with Gabriel and Balthazar in tow. It had been a slight hassle to get them to come but Cas had won out.

Dean was busy in the kitchen with Ellen and Jo. Bobby and Sam were at the table, Bobby with a beer in hand. Gabriel and Balthazar went to sit on the couch.

“Hello, Dean,” Cas said, walking up next to him in the kitchen.

“Hey, Cas,” Dean said, “want to help me with these potatoes?” 

Cas laughed and politely declined. He wasn’t very helpful in the kitchen so he joined Bobby and Sam at the table. 

“Hi Sam, Bobby,” Cas greeted.

“Hi, Cas,” Sam said while Bobby just nodded.

Once dinner was finally ready, they sat down at the usual table and one they had dragged over from Bobby and Ellen’s apartment.

Cas sat next to Dean and across from Gabriel and Balthazar who, once they opened up and made conversation, actually got along with everyone. Gabriel play flirted with Sam. Balthazar and Jo had already built a sarcastic banter.

It was amazing. Cas turned to share a smile with Dean.

“I’m glad you invited us, Dean,” Cas said softly.

“Me too,” Dean grinned. “Wouldn’t have been right not having you here.”

It was a good thing Cas was a lefty and Dean was a righty so they could hold hands under the table while they ate. 

 

It was the first weekend in December and Dean was driving with Cas in the Impala. 

Cas sighed contently as they drove, glad Dean had asked him out. 

“What?” Dean asked with a little smile.

“I’m just… happy. I’ve missed this… the car…”

“Did you miss my car more than me?” Dean joked, his smile getting bigger.

“Maybe,” Cas teased, grabbing Dean’s hand that wasn’t on the steering wheel. 

“You still don’t know where we’re going,” Dean pointed out, squeezing Cas’s hand.

“I’ve learned to have faith in your surprise dates, Dean,” Cas said. 

They drove up and parked outside the Museum of Science and Industry. 

“Dean…” Cas grinned.

“Now you can show me everything here you wanted me to see,” Dean said, smiling back. Cas pulled him in for a quick kiss.

“Let’s go,” he said excitedly. 

Cas practically dragged Dean into the museum but Dean didn’t mind. He knew that’s what Cas would do. They wandered around inside for hours, looking at everything. Not surprisingly, Cas did know exactly which exhibits Dean would want to see.

“You’re amazing, you know that?” Cas said, watching Dean read a sign going with an exhibit, his lips moving just a little.

“I… what?” Dean asked, turning just a little red.

“You heard me,” Cas said, playfully bumping his shoulder against Dean’s as they kept walking.

“Well, you’re pretty amazing yourself, Cas,” Dean smiled. It was a wonderful and warm smile and it was just for Castiel who tried his hardest to memorize it.

The two of them stopped to get some pizza before heading home. 

Dean asked Cas if he wanted to come over. Cas was confused only because he didn’t know if Dean was sure.

“I mean… if you want or…” Dean stammered.

The apartment was empty because, as the note they found said, Sam and Jess went to study even though it was a Saturday. 

“What a nerd,” Dean said. Cas laughed.

“So… should we…watch a movie?” Dean asked. Cas agreed and they sat on the couch, choosing to watch _Say Anything._

“You know, that would have worked,” Dean said as the main character stood under the window with a boombox.

“Oh, really?” Cas asked. He was curled against Dean, his head on his chest and Dean’s arm around him.

“Yup. You could have showed up and BAM!” Dean said, snapping his fingers on the last syllable.

“And what song would have you preferred?” Cas said, playing along with the joke. He sat up enough to be able to look at Dean.

“Oh, I think you know,” Dean winked.

“Faithfully?” Cas asked, remembering it was their song. 

There had been plenty of times he fell asleep listening to that song over the summer, looking for comfort he couldn’t find. The song wasn’t as important as who he thought about when he heard it. 

“Wondering where I am, lost without you. And being apart ain’t easy on this love affair,” Dean sang, easing Cas back against the couch, movie forgotten.

“Two strangers learn to fall in love again,” Cas sang the next line, letting Dean press his weight slightly down on him. 

“I get the joy of rediscovering you,” Dean continued, mouth inches from Cas’s, distracting him from finding the words. 

“Oh, Cas,” Dean sang and Cas let out a soft laugh at the replaced word, “you stand by me.”

“I’m forever yours,” Cas sang, remembering the words now.

“Faithfully,” they ended together. 

Dean pressed his lips against Cas’s completely. Cas made the smallest moan which, in turn, caused Dean to kiss him with more fervor and lick his tongue in Cas’s mouth. They took the time to relearn each other’s mouths gently and slowly.

Dean had one hand on Cas’s cheek and the other on his hip. Cas had one hand lifted into Dean’s hair and the other grabbing at his shirt between his shoulder blades.

When they broke for air, Cas laughed a little. 

“What?”

“Nothing, it’s just that another _Journey_ song seems to fit our situation, too,” Cas explained. 

Dean still looked confused. 

“Open Arms?” ‘Wanting to hold you, wanting you near, how much I wanted you home. Now that you’ve come back, turned night to day, I need you to stay. Hoping you’ll see what your love means to me,’” Cas said, instead of sang, as he ran his fingers through Dean’s hair. He put as much sincerity into it as possible as he looked into Dean’s eyes.

“I guess that does fit,” Dean said, blushing a little, “Love, huh?”

“Of course,” Cas said, squinting and tilting his head.

“I missed that,” Dean said, kissing Cas sweetly on the nose before continuing to kiss him on the lips. “And you. God, I missed you so much.”

“I missed you, too, Dean,” the last syllable slightly groaned as Dean began to kiss a sensitive spot on his neck. 

Dean’s hand on Cas’s waist started to go under his shirt and Cas mirrored him. Dean did the slightest roll of his hips, making Cas moan his name and throw his head back against the couch.

“Fuck, Cas, little warning next time.”

“I could say the same thing.” 

“We should journey to the bedroom,” Dean said, not moving until Cas agreed.

“That was maybe the worst way to ask that,” Cas said but with a smile, “just terrible.”

“I thought you’d appreciate it,” Dean said also smiling. He got up off the couch and helped Cas up to lead him into the bedroom and shut the door. 

Cas took control once the door was shut, pinning Dean against the door. His hips and chest were flush against Dean as he sucked a bruise on his neck. Dean ran his hands through Cas’s hair before Cas grabbed them and pinned them against the door above their heads.

“Jesus, Cas,” Dean moaned as Cas continued kissing his neck before returning to his lips. 

The kept kissing, backing away from the door to the bed, pausing only to take off their shirts. Kissing resumed and they ran their hands over the other one’s bare chest, remembering the muscles and skin. Dean let out a sharp breath when Cas’s hand rubbed a nipple which made Cas break the kiss and smile mischievously. His other hand ran up Dean’s abdomen and chest to lightly squeeze the other nipple. 

“Cas…” 

They reached the bed and Cas pushed Dean onto his back. They each paused to breathe and take in what was going on for just a moment before Cas crawled on top of Dean, their lips crashing together. Cas rolled his hips like Dean had done earlier and Dean groaned into Cas’s mouth. Cas kissed more heatedly and moved his hips with more determination, feeling Dean getting hard underneath him. 

With sloppy desperation they worked their pants and briefs off, pausing again to rememorize each other.

“You’re fucking gorgeous, Cas,” Dean said, out of breath and under Cas still. 

“And you are beautiful, Dean,” Cas returned the compliment, eyes raking up and down every glorious inch of perfect body. “Do you…”

“Yeah,” Dean answered, “same place.”

Cas knew where to go, top drawer of the nightstand, for what he needed. Dean momentarily missed the heat and weight of Cas on top of him until he returned with the condom and lube. Dean could guess what Cas wanted and he grew harder and hotter at the thought. 

“Dean…”

“Cas, please, yes. God yes.”

“You don’t know what I was going to say,” Cas protested with a frown.

“Yes, I do,” Dean insisted. “Just fuck me.”

Cas wasted no time. He prepped a finger with lube before easing it inside Dean. As he slowly moved in and out, Dean let out a noise close to a hiss. Cas pressed their mouths together before trailing kisses down Dean’s body, stopping at his hips, his finger never stopping. As he sucked down on Dean’s cock, he slid a second finger in and starting working Dean open.

“Ca-aas,” Dean whined, his voice catching. Cas watched him come undone, looking up as he continued to move his mouth and fingers. Every noise Dean made got him harder until it was almost too much. After a third finger and more motion, he released Dean’s dick from his mouth. 

“Are you…”

“Yes, please, fuck me Cas,” was the response. Cas rolled the condom on and applied lube generously before sliding into Dean with a snap of his hips and Dean let out a yell.

Cas built up his rhythm and held onto Dean’s hips.

“Dean, touch yourself,” Cas demanded. Dean did. He left one hand on Cas’s shoulder and the other began to work himself in long, deliberate strokes to match Cas’s rhythm, even as he sped up more. 

“God, Dean. I’ve wanted this, you under me, for so long time.”

“Fuck,” Dean moaned, eyes closing as he got closer to the edge. 

“No, look at me,” Cas said. Dean opened his eyes. “Look at me when you come.”

Cas knew Dean was close when he watched his hand falter. Dean came over his stomach, yelling Cas’s name. Cas continued to thrust into Dean until he came inside him. He pulled out and collapsed next to him, rolling off the condom and throwing it into the garbage like he’d done countless times before. He then grabbed a shirt and cleaned off a very spent and tired Dean.

“Damn, Cas,” Dean said, still out of breath. Cas curled up against his side and laid his head on his bare chest. “Where’d you learn to be so good?” 

“Everything I know I learned from your encouragement.”

“I am fucking amazing then,” Dean joked. Cas playfully hit him on the stomach. 

“I love you,” Cas said, starting to feel sleep grab hold. 

He was afraid maybe it was too soon for that but squashed the thought. It felt right.

“I love you, too,” Dean said, gripping Cas tighter and tilting his head up to kiss him once more before they fell asleep.


	15. Chapter 15

Cas and Dean spent every night together after that. Sometimes they had sex, sometimes it was just nice to hold each other after they had been apart for so long.

As Christmas approached, Cas thought of something as he and Dean were in the Impala heading to lunch. 

“This is our first Christmas together,” Cas noted. 

“Hmm,” Dean hummed thoughtfully, “I guess it is.”

“So, I mean… we haven’t been back together for very long,” Cas observed. “Do we want to do… presents?” 

The morning after they had sex for the first time since Dean had been out, they decided the wait was over and that they were officially dating again. There were still some times that Cas could tell Dean was a little hesitant and he was patient with him. Forgiveness was a long road and Cas would wait.

It was all he wanted, to be dating Dean so he could kiss him and hold him and take him out.

“Like, get each other presents?” Dean asked. Cas nodded. “We can if you want.”

“Well, neither of us have a lot of money and…”

“We don’t have to if you don’t want to Cas,” Dean said, “it’s not a big deal.”

Cas nodded. He kept thinking of what he would have gotten Dean if they chose to do presents while they ate lunch. There were plenty of things he thought of but nothing seemed good enough.

Dean had picked Benny’s diner for lunch. Benny had come home a week ago but was having a hard time adjusting. Andrea had finalized their divorce once Benny was home and he was taking it pretty hard. 

They had chosen to eat here to check on him. He seemed okay, at least on the outside, as he flipped burgers in the back.

The two tried as hard as they could to not rub their rekindled relationship in his face. 

 

~~~

 

The following Saturday, a week before Christmas, Gabriel dragged Castiel out shopping. 

“Seriously…why do we have to come to the mall? At this time of year?” Cas complained. Sure the lights and decorations were nice and the Santa in the center of the mall was a nice touch but parking had been a nightmare and the amount of people crowding the building was practically suffocating Cas. 

“I told you,” Gabriel said, “I need a gift for a special someone, new girl at the candy shop where I work.”

“Right,” Cas rolled his eyes. “Kali.”

“Don’t give me that,” Gabriel snapped, “don’t you need something for Dean-o anyways?”

“Dean and I aren’t doing gifts.”

“Sure,” Gabriel smirked, “how much you wanna bet he gets you something anyways?” 

Cas paused to think about that. He supposed it was possible that Dean would buy him something, even a little gift, because that’s how he was. Also, even though he had said it wasn’t a big deal, Cas knew that Dean liked Christmas. A holiday all about family was perfect for him and he could cook another big, delicious meal. 

Cas sighed. 

“So, you’ll get him a present?” Gabriel prodded as they wandered into a jewelry store for his mystery lady. 

“If I see something while we’re here, maybe,” Cas conceded. 

And he did. He saw the perfect gift he could get Dean. They were passing a shoe store, a small one, when Cas saw the perfect pair of boots. Cas couldn’t help but notice the wear and tear on Dean’s current pair and he knew that he had had them for a long time. This pair was a similar shade of brown, sturdy looking and just right.

“Gabriel, stop,” Cas commanded, dragging his brother into the store.

“Are you sure you want to spend that much?” Gabriel asked as Cas handed over his card. It would be a significant slice out of his account but it would be worth it. He smiled as he tried to picture Dean’s face when he would open them on Christmas. 

 

~~~

 

On Christmas Eve, Cas was at Dean’s watching Christmas movies with Sam and Jess. The four of them drank eggnog, Dean’s with a powerful kick, and ate cookies Dean made along with some Jess had brought. 

Once Jess and Sam turned in for the night, Dean wasted no time practically crawling on top of Cas. He whispered in his ear that he wanted to do this all night before he kissed him. Cas kissed back just as eagerly before they quickly moved to Dean’s room. Dean let Cas take control and they had slow, passionate sex. 

After, Dean noticed his bedside clock read that it was past midnight.

“Merry Christmas, Cas,” Dean said with a silly, content smile as his eyes closed. 

“Merry Christmas, Dean,” Cas said back, kissing Dean on the forehead before settling between his arm and chest and falling asleep. 

Cas slept so much better with Dean than alone and it was really helping his overall health. It didn’t go unnoticed by Cas that Dean had quit smoking and that was certainly doing him favors, too.

 

~~~

 

The next morning, Christmas morning, Dean and Cas were woken up by knocking on their door. Very loud knocking. 

“Are you two decent?” Sam called. 

“No, we’re completely naked,” Dean yelled back honestly. Cas laughed into the pillow but didn’t open his eyes. 

“Oh, come on! Seriously? Get dressed, it’s Christmas you two!” Sam yelled back. 

“He better be making coffee,” Cas grumbled into the pillow as he heard Sam’s footsteps retreat. 

Once they did get dressed, they walked out to join Sam and Jess to open presents. Apparently, Jess wanted to avoid her mom’s new boyfriend and convinced her to let her stay with Sam but she would have to go back for dinner. 

They began to exchange presents. Dean and Cas took the couch and Sam and Jess sat on the floor. They had a little Christmas tree set up on the coffee table. Sam and Jess had each gotten the other one a Stanford hoodie and claimed they had no idea what the other was planning. 

“We’re not that gross are we?” Dean asked, leaning in to whisper in Cas’s ear as Sam kissed Jess over the pile of wrapping paper they made. 

“I hope so,” Cas said, kissing Dean. It was quick and they broke with a smile.

“All right, all right,” Sam said, “Dean, here’s your gift.”

Sam had gotten Dean a cookbook and Dean got Sam the boxed set of all of the Star Wars movies. 

“We’ll have to marathon sometime. Thanks, Dean,” Sam said with a grin. Dean nodded. 

“Cas, I got something for you here,” Dean said, getting one of the two remaining presents under the tree and handing it to Cas. 

“The last one is for you,” Cas said. 

“And we said we weren’t doing presents,” Dean smirked. Cas just bumped him with his shoulder in response.

Cas got a brand new journal with a leather bound cover. 

“For, you know, writing,” Dean said, rubbing the back of his neck, “and stuff.” 

“I love it, Dean,” Cas said, slightly overwhelmed. It was perfect. The only thing that topped it was Dean’s face when he opened his new boots. There was shock, joy, excitement… everything Cas hoped he would see.

“These are perfect,” Dean smiled, leaning over on the couch to kiss Cas. He reached up to grab the back of Cas’s neck and was getting more passionate when Sam cleared his throat. 

“Don’t you have food to start making?” Sam asked with an amused look. 

“Shut up,” Dean said, grinning and not looking away from Cas. 

 

Dinner was a lavish affair. Bobby, Ellen, Jo, Gabriel and Balthazar all showed up and so did Benny. There was ham, potatoes, a variety of vegetables, rolls and salad. That was all before the pie. 

In a post-dinner food coma, Dean sat with an arm around Cas. It was cozy and warm as they all watched Christmas movies on TV. 

“This is the best Christmas ever,” Dean said. 

“Yeah?” Cas asked, turning to look at Dean. 

“Yeah.”

“Me too,” Cas agreed. They kissed, briefly, but Jo still yelled at them to get a room. 

“It’s my apartment!” Dean grumbled. That got a laugh and Cas playfully squeezed his knee. 

“What’s family for?” Cas said quietly, just for Dean. A look of understanding passed over his face. Dean got that Cas thought of everyone here as his family and that he wasn’t going anywhere. 

Definitely the best Christmas ever. 

 

New Year’s was a relaxing event at the Roadhouse. Dean didn’t end up drinking too much and Cas got the midnight kiss he had been dreaming of. He kept that fantasy so wrapped up he never even told Dean but he didn’t too. It only made sense that Dean kissed him at midnight. 

Benny got drunk enough that he kissed Jo at midnight and shockingly left the party alive because Jo obviously kissed back. Afterwards, Ellen glared and Bobby threatened but all in good fun. Proabably. 

Gabriel had brought Kali, Sam was with Jess and Balthazar somehow managed to bring two women. Cas couldn’t remember either of their names but he figured he wouldn’t be seeing them again. 

Before they knew it, Cas and Dean had been back together for two months and it was Dean’s birthday. Cas treated him to dinner at Giuseppe’s followed by making out like teenagers in the backseat of the Impala. 

Cas had bought Dean a few new little trinkets and utensils he needed in the kitchen and a new plaid shirt.

“Right,” Sam had rolled his eyes, “because he doesn’t have enough of those.”

“You have enough plaid, too,” Dean retorted before kissing Cas to say thanks. 

After relaxing and watching Dean’s picks of movies, Dean had taken a pause to take out the garbage after he got up to throw out another empty beer bottle and saw how full it was. 

Cas glanced at his watch after Dean had missed his favorite part of Braveheart, the big speech. His stomach sank as he realized it had been ten minutes. 

“Sam, I think something’s wrong,” Cas said, running out the door without hesitation. He practically flew down the stairs and out the side door to the alley. He heard a small, pained moan and followed it to the source.

Slumped against a dumpster was Dean. His eyes were closed, face bloody and he was holding one arm tight to his body. Cas froze for a split second before he went into action.

“DEAN!” Cas yelled. He ran and dropped to his knees next to him. “Dean, hey, look at me.”

He opened his eyes slowly.

“Cas?” he asked, dazed. 

“Come on, we have to get you inside, it’s freezing,” Cas said. Dean already felt very cold. Cas gently got a shoulder under one of Dean’s arms and helped them both up and inside. It was a painstaking effort to get to the elevator and up to the apartment but they managed. 

“Holy shit, Dean,” Sam said, jumping to his feet. “How does this keep happening?”

“Wish I knew,” Dean said with a wistful smirk before coughing and wincing in pain. 

“Dean, try to keep quiet,” Cas said, gently laying him down on the couch. “Save your strength.”

“What happened?” Sam asked.

“Crowley,” Dean said. He passed out almost right after he said that and Sam and Cas let him sleep. 

“Crowley?” Sam asked at the table. “Isn’t he in jail?” 

Cas sat across from Sam, his eyes on Dean. They had cleaned the cuts on his face and guessed his shoulder was dislocated. His side was probably going to be badly bruised but his ribs didn’t seem cracked or broken.

“I guess he’s out,” Cas said. 

After an hour of being out, Dean came around with a cough and then what sounded like “ow, fuck.”

“Dean,” Cas exclaimed before going to his side and kneeling next to the couch.

“Happy fucking birthday to me,” Dean said, attempting to grin and joke. 

“What do you mean it was Crowley?” Sam wanted to know. 

“I mean it was Crowley,” Dean rolled his eyes, “he’s out, said there was an error in the trail or evidence or something. He’s out on a god damn technicality. He threatened me. And you two. I guess he’s pissed he got arrested and his little drug ring got busted.”

“He couldn’t believe I was back with you,” Dean added, taking Cas’s hand. “After… well, everything. I told him to fuck himself then he beat me up. All the beer I had slowed me down. But don’t worry, I got in a few good swings.”

“So, do we go to the cops?” Sam asked. 

“No, Sammy, I’m fine.”

“But…” Cas tried.

“I’m fine,” Dean insisted. “Seriously, I’m not scared of Crowley. I can take him usually. He just kind of caught me off guard.”

Cas and Sam shared a look, knowing it was stupid to not go to the cops but they also knew how stubborn Dean was and that there wasn’t any way to change his mind. 

 

The subject was pretty much dropped while Dean spent the next week and a half recovering. The worst was the shoulder, even after Sam popped it back in because Cas just couldn’t do it. 

As Dean and Cas drove one night, Dean was actually the one to bring it up again which surprised Cas. He had mostly been avoiding the subject. 

“So, I was thinking about the whole Crowley thing…” Dean started, looking sideways to see that Cas was paying attention. Of course he was, eyes solidly on Dean. Dean cleared his throat, struggling to find the right words here. 

“Dean, whatever it is, you can tell me. We’ve been through much together, you and I,” Cas said gently, trying to coax whatever Dean was trying to say out of him. 

“I know. And that’s it. So much has happened here, good and bad. But after Crowley I guess I just see the bad. And… well, I was thinking of moving out to, uh… California. By Stanford, when Sam goes. Kind of a fresh start, you know?” 

“Oh,” Cas said in a small voice. 

Instead of looking at Dean, he was looking in his lap. It was a repeat of Dean telling him to get out after he learned the truth about him being an informant what felt like ages ago. The world was collapsing and there was nothing to do to fix it. 

“It would be good, I think. Bobby has a friend out there who has an auto shop, Rufus or something and I could keep doing what I do best. Cas, you look like you’re going to throw up, are you okay? Please do not puke in my baby,” Dean continued. 

“I…I’m fine,” Cas managed weakly. 

“No you’re not,” Dean said, pulling the car over and putting it in park. “What’s wrong? Dude, this is good news!” 

“For you, maybe,” Cas whispered. 

“What?” Dean asked. “What are you talking about?”

“You’re leaving. To go with Sam. To California. That’s great, for you, but what about me?” Cas said, his voice still soft and unable to look at Dean. 

“Oh,” Dean said with understanding. “ _Oh_ , Cas, oh my god.” 

Dean started laughing. Cas turned to glare at him. He couldn’t fathom what Dean could find funny right now.

“Dean…”

“You big dummy, you’re coming with! If you want to, I mean.” He added the last part in a haste. 

“What? Dean, are you serious?” Cas asked, his face knit in confusion, head to the side.

“Yeah!” Dean answered enthusiastically. “Of course! Come with me to California. What do you say, Cas?”

Cas looked at Dean’s big smile and bright green eyes and said the only logical thing he could. 

“Of course, Dean.”

 

Castiel waited until the beginning of February to tell Gabriel and Balthazar his plan to go with Dean to California. After all the crap they had been through growing up, it was hard to imagine not living with his brother and it took him over a week to build up the courage to tell him he was moving across the country.

Gabriel took it shockingly well. 

“My little baby bro is growing up!” Gabriel said, pretending to wipe a tear off of his cheek. 

“You’re not mad?” Cas asked, ignoring the baby comment.

“Of course not! I mean, I’m gonna miss you like hell but I’m not mad. I’m glad you’re going with Dean, he’s the best thing that ever happened to you even with all the shit you put each other through.”

“Don’t I know it,” Cas said. He smiled and gave Gabriel a hug. 

It was a similar reaction when Cas told Balthazar who was like a brother to him now. There was a giant weight off of Cas’s chest when they finally knew. 

 

Dean and Cas decided, in addition to work, they would try to finish their GED’s again so they returned to Pamela Barnes’ class. She only teased them a little for not finishing earlier. 

Once they got started with that, there was a comfortable routine they fell into. Dean drove Cas as much as he could when they went to work at similar times and would pick him up as often as possible, too. They never missed a class with Pamela and they were both doing well. 

The two of them alternated where they slept but it was always together. Sam and Gabriel both got very used to seeing their brothers’ boyfriends in their apartments, more than usual. Gabriel liked when Dean stayed over because he made breakfast for all of them. 

Aside from that, Dean worked on building up the courage to tell Benny he was leaving. They had been thrown into the same crappy situation and fought it out together and it would be weird not to see him all the time. Cas helped by telling Dean that when he told Gabriel and Balthazar, it made him feel better and made it feel more real, that it was actually happening. 

Dean took Benny to the Roadhouse to break the news. 

“So… you’re going to California with your brother and your boyfriend,” Benny said slowly, taking it in after Dean told him. 

“Uh, yeah. Listen, I know…”

“Hey, brother, I’m happy for you. Honestly,” Benny said, cutting Dean off. Dean smiled in relief. 

“It is good to hear you say that.”

“Besides,” Benny said, looking at Jo behind the bar, “I think I’ll manage without you.”

Dean laughed when Benny looked away after a glare from Ellen who was next to Jo at the bar. Jo smiled as she filled drinks for a table.

“Her mother though…”

“Terrifies me,” Benny agreed with a laugh.

 

Before they knew it, it was already early June and it was time for Sam to graduate. Cas and Dean had also finally finished up their GED’s but wanted to keep the focus on Sam.

“Dean, you accomplished something big too,” Sam insisted. 

“It’s not about me, man. You finished high school and got a full ride to an awesome school. Let me get a good look at you,” Dean said, effectively brushing his brother off. Sam took a step back so Dean could look at him in his cap and gown.

“I’m proud of you, Sammy,” Dean said, “Mom and dad would be, too.”

They shared a brief hug before heading to the graduation, picking up Cas on the way. Jess would be showing up with her family and Ellen, Bobby and Jo would meet them there.

The ceremony was long and it was hot outside in the school’s stadium. Dean cheered obnoxiously loud for Sam when they called his name to get his diploma even though it was supposed to be just a quick clap for each person. Cas expected that and laughed.

After countless pictures at the school, they came back to Sam and Dean’s apartment to celebrate. Cas helped Dean get the snacks and few other things he had made from the kitchen area. 

“It’s like diffusing a bomb,” Dean said as he struggled to pull the cork out of a bottle of champagne. Cas tried to hide his laugh but Dean caught him. 

“You do it then,” Dean said. Cas took the bottle and opened it easily. 

“Of course,” Dean said with a dramatic eye roll. “Well, I loosened it for you.”

“Sure,” Cas said. He kissed his boyfriend on the cheek, making him turn just slightly red, before taking the champagne to the table where Ellen and Bobby waited with glasses.

The celebration was fun but eventually Ellen, Bobby, and Jo went home. Cas had already planned on staying the night but didn’t really to bring anything over. He had enough of his own extra clothes here and a spare toothbrush as well. 

 

A couple days later was the big move. The Impala was packed with all of their stuff, which was mainly a few suitcases and duffels filled with clothes. Sam wanted to get an early start and take some summer classes so off they went. 

It was a long drive, thirty-two hours, but they made plenty of stops for Dean to try burgers across America.

Once they got Sam settled into his dorm, they headed over to Cas and Dean’s new one bedroom apartment. The three of them immediately noticed it was a lot nicer than either of their apartments in Chicago. It had been listed as move-in ready and sure enough had all the furniture they would need. 

They dropped their bags down and went shopping for food. Back at their new home, Dean started making pasta for the three of them. After an amazing dinner, Dean’s words but Cas and Sam agreed, they brought Sam back to his dorm.

“All right, Sam,” Dean said, pulling his brother into a hug, “be good. Call if you need anything, we’re super close, we can be here in like… 5 minutes. Tops.”

“I’ll be fine, Dean,” Sam laughed, “and I’ll call if I need anything.”

“Promise?” 

“Promise.”

Cas hugged Sam as well and said he’d see him again soon. Cas and Dean got back into the Impala.

“Let’s go home,” Dean said, grinning as he started the car. 

“I like that. Home,” Cas grinned back. 

“Me too.”

 

~~~

 

The summer was wonderful and passed quietly and blissfully. The lack of gangs, drugs and violence was a welcome change to their lives. They almost didn’t know how to handle their stress-free lives. 

Dean began working for Rufus at his auto garage and would come home to Cas with stories of the guys he worked with. Rufus was grumpy and knew cars well and was similar to Bobby. Ash was great, a genius really, and pretty good with cars, though not as good as Dean as he would always point out. Garth was kindhearted but when he worked, Dean had to take a lot of time fixing his mistakes but he helped him learn.

Cas signed up for a few creative writing and English classes in the fall at Stanford and was currently working at their library. He loved books and couldn’t be apart from them. There were also a lot more people that come through this library than the Chicago community college he was used to but that just gave him more to write about. He had almost filled up the journal Dean had given him for Christmas.

The apartment was really starting to feel like home and neither Cas or Dean felt like changing anything about their current situation. Being able to fall asleep in each other’s arms and wake up together in a place all their own was comfortable and special at the same time. 

Sam and Jess lived in the same dorm building and studied constantly which Dean and Cas expected. They even planned their schedules so they could take some general education classes together. 

They all missed people from back home, so when Thanksgiving came around it was a relief to be heading back. Sam had convinced Dean to fly home, with help from Cas, so they could spend more time with people they loved and cared about rather than driving the whole time they were off of work and school. 

“But what about my car?” Dean whined as they took a taxi to the airport the day before Thanksgiving. 

“It’ll be fine in the parking garage, I told you. No one will touch it,” Cas said. After that, he was still nervous about flying. 

“Honestly, your first flight can be rough but you’ll be fine,” Jess assured him with her winning smile. 

It went well enough once Dean ordered whiskey on board and he nearly squeezed the life out of Cas’s hand but they landed before he knew it.

“See, that wasn’t so bad,” Cas said, kissing his cheek as they walked to another taxi. 

The four of them got to Bobby’s and there were hugs all around from Ellen, Bobby, Jo and Benny. It was a little weird for Sam and Dean being in their old building but not actually living there like they had their entire lives. 

Ellen offered to bring Jess and Sam over to Jess’s parents’ place, where they were staying, to drop their stuff off so they did. Dean and Cas would be sharing Ellen and Bobby’s pull-out couch. 

“How’s Rufus?” Bobby asked, offering Dean and Cas beers which they accepted.

“Ornery as hell,” Dean answered.

“I thought so,” Bobby said. “That old nut.”

Dinner the following day was warm and delicious like the previous year, with the same family present. Gabriel and Balthazar both nearly crushed Cas when they came over and finally saw their baby brother.

“Oh goodness, look at you,” Gabriel said. Surprisingly, Gabriel hadn’t messed things up with Kali and she showed up, too. 

“You better be taking care of him,” Balthazar said, pointing a finger at Dean who threw his hands up in surrender.

“He is,” Cas assured. 

After a huge and filling meal, they all sat around watching TV in the usual food coma. 

“I’m never eating again,” Cas complained, his cheek warm against Dean’s sweater as he curled up against him on the couch.

“You better be,” Dean said, rubbing circles on Cas’s back, “we have a date tomorrow. We’re going to Giuseppe’s.”

“Oh,” Cas said, then laughed a little.

“What?” 

“I made a reservation, too,” Cas explained then they laughed together. 

 

“It’s been kind of weird having to be so adult, you know?” Dean said as they ordered an appetizer. Cas always insisted they get calamari and his face was too cute for Dean to say no. Plus, he was starting to actually like calamari. 

“Well, you are twenty-two, Dean,” Cas pointed out. Dean rolled his eyes with a good natured smile.

“Parts of it have been nice, too,” Dean said.

“Yeah? Which parts?” Cas said with a sly grin he tried to hide as he drank his water.

“Living with you is awesome,” Dean said, rubbing the back of his neck, “like cooking for you and driving you to work and hearing what you’re working on for class. It’s awesome.”

“It’s been awesome living with you, too, Dean,” Cas smiled, “I love sharing everything with you, hearing your stories and you are getting even better at cooking than before.”

Cas grabbed one of Dean’s hands across the table until their calamari came and they ordered their entrees. 

They ate and talked and laughed. Dean knew with certainty what he was about to do was the right thing. Their desert came and he talked while Cas ate.

“Cas, I brought you here…for a specific reason. And you know, um, that I suck at words and feelings or whatever. But I know that you are the best thing that’s ever happened to me and I want to spend the rest of my life with you,” he said, clearly nervous and red in the cheeks. 

He got on one knee and Cas almost choked on the cake he was eating. Dean waited for him to swallow and take a sip of water before he continued. 

“Castiel Novak, will you marry me?” Dean asked as he pulled a box out of his pocket and opened it to reveal a gold ring.

“Oh my god, Dean,” Cas said, barely loud enough for Dean to hear. He stared at the ring and seemed to forget how to form words.

“Um, Cas?” Dean asked, getting awkward kneeling on the restaurant floor. 

“What? Right! Of course, of _course_ , Dean. Yes!” Cas answered enthusiastically. Dean slid the ring on Cas’s finger and kissed him amidst polite clapping from other people in the restaurant.

When he sat back down, Dean took a gulp of water because his throat had gotten very dry.

“Sam helped me pick it out. And he told me I would be an idiot if I didn’t ask.”

Cas looked at his ring and laughed a little. 

“What?” Dean asked with a mouthful of cake. 

“Gabriel helped me, too.”

“With what?” 

“Dean, you’re the best thing that’s happened to me, too. I know we’ve had some rough patches,” Dean snickered at that, “but one thing is certain. I want to spend the rest of my life making up for my mistakes. I want to be with you no matter what.”

It was Cas’s turn to get on one knee and it was lucky that Dean wasn’t eating cake or he would have choked, too. 

“Dean Winchester, will you marry me?” Cas asked as he too pulled out a box showcasing a gold ring. 

“Yes, Cas,” Dean said with a huge smile. Cas did the same thing Dean did, put the ring on and kissed him. 

“Wow, great minds do think alike,” Dean said, looking at his finger with a new ring. 

“You’re still such a sap,” Cas rolled his eyes. 

“And so are you,” Dean answered. 

The prospect of forever weighed on them but held so much promise and happiness that it didn’t feel like a weight at all. 

Cas grabbed Dean’s hand across the table again as they finished their cake. 

“You know, you’re going to be stuck with me forever right?” Dean joked. 

“That’s kind of what I’m hoping for,” Cas smiled, “I’m forever yours.”

“Faithfully.”


End file.
